EP1714140A1 - Hochselektiver chemischer tandem-sensor und nachweisverfahren damit - Google Patents
Hochselektiver chemischer tandem-sensor und nachweisverfahren damitInfo
- Publication number
- EP1714140A1 EP1714140A1 EP05716653A EP05716653A EP1714140A1 EP 1714140 A1 EP1714140 A1 EP 1714140A1 EP 05716653 A EP05716653 A EP 05716653A EP 05716653 A EP05716653 A EP 05716653A EP 1714140 A1 EP1714140 A1 EP 1714140A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- detected
- molecules
- type
- fluorescent material
- sensor according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000126 substance Substances 0.000 title claims abstract description 27
- 238000001514 detection method Methods 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 48
- 239000002861 polymer material Substances 0.000 claims abstract description 9
- 238000012546 transfer Methods 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000003795 desorption Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 239000011325 microbead Substances 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229920000344 molecularly imprinted polymer Polymers 0.000 description 7
- 229920001109 fluorescent polymer Polymers 0.000 description 6
- 239000002360 explosive Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic nitro derivatives Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000321453 Paranthias colonus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003592 biomimetic effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010897 surface acoustic wave method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
- G01N21/783—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour for analysing gases
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/7703—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator using reagent-clad optical fibres or optical waveguides
- G01N2021/7706—Reagent provision
- G01N2021/773—Porous polymer jacket; Polymer matrix with indicator
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N2021/7756—Sensor type
- G01N2021/7763—Sample through flow
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N2021/7769—Measurement method of reaction-produced change in sensor
- G01N2021/7786—Fluorescence
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2600/00—Assays involving molecular imprinted polymers/polymers created around a molecular template
Definitions
- the field of the invention is that of chemical sensors and in particular sensors capable of detecting particularly dangerous molecules such as explosives, drugs ...
- a chemical sensor comprises a sensitive layer brought into contact with a transducer which translates the signal chemical generated following interactions between the sensitive layer and the compound to be detected in an easily quantifiable signal.
- An effective chemical sensor must therefore fulfill the following two conditions: being able to easily create interactions with the molecule to be detected and generating an easily observable signal.
- a very large number of technological solutions in the field of gas detection are available today. However, there is not yet a system which combines high selectivity, very high sensitivity and very short response time for the detection of dangerous gases.
- the selectivity is only partial since a priori many molecules of electron deficient type can extinguish (quencher) the fluorescence of the polymer and therefore lead to false alarms.
- quencher quencher
- the potential interferers can be fragrances, some of which are shown below.
- Nitrobenzene a tobacco by-product, can also falsify detections.
- the present invention provides a highly selective chemical sensor combining the detection of molecular entities by a variation in fluorescence and the prior selection of said entities by a chemical filter based on molecularly imprinted material.
- the invention proposes a new concept of sensor in which we associate a material which will sort the molecules ( filter) with a fluorescent material which will act as a sensitive layer. It should also be noted that in this way, the risks of saturation of the sensitive polymer are also limited following the adsorption of interfering molecules.
- the subject of the invention is a chemical sensor intended for the detection of a type of molecule comprising a fluorescent material capable of forming a complex with the type of molecule to be detected and means for measuring the variation in fluorescence of said material, characterized in that it further comprises a filter comprising a polymeric material comprising so-called molecular fingerprint cavities whose geometric and chemical configuration is defined so as to fix only the type of molecule to be detected.
- the fluorescent material may be a polymer or a set of small molecules.
- the fluorescent polymer may be a polymer with a pi-conjugated chain, for example of the type
- the polymer material comprising so-called molecular fingerprint cavities can be obtained from functional monomers capable of complexing the molecule to be detected, the interactions possibly being of the hydrogen bond type,
- the fluorescent material can be deposited in a thin layer on the surface of at least one first substrate.
- the polymer material comprising so-called molecular finger cavities can be produced on the surface of a membrane or on the surface of microbeads so as to provide a maximum exchange surface with the outside and so as to also allow a response time. (adsorption time of molecules to be detected) as short as possible. More precisely, it can be formed on the surface of a membrane or on the surface of microbeads maintained in a porous support, positioned perpendicular to the charged flow or positioned parallel to the gas flow and arranged in a column of the chromatographic column type.
- the senor can comprise a pump for sucking in an external medium charged with the type of molecule to be detected. It can also include a source of inert gas which may be nitrogen, positioned downstream of the pump to transport the molecules to be detected to the polymeric material with cavities. According to the invention, the sensor can also comprise a removable shutter making it possible to separate the polymeric material with cavities from the fluorescent material.
- the means for detecting variation in fluorescence may advantageously comprise a light source for illuminating the fluorescent material and photodetection means for collecting at least part of the light emitted by the complex formed between the fluorescent material and the molecules to be detected, or to measure the decrease in the light emitted by the “raw” material following the adsorption of the molecule to be detected, ie following the formation of the complex.
- the subject of the invention is also a method of chemical detection of a type of molecule by a sensor according to the invention, characterized in that it comprises the following steps: - the capture by selective adsorption of the type of molecules to be detected by the polymer material comprising so-called molecular finger cavities.
- the type of molecules to be detected can be captured with a pump so as to collect a flow external to the sensor loaded with molecules to be detected.
- the method can comprise closing a shutter making it possible to isolate the polymeric material comprising cavities, from the fluorescent material, during the capture operation. It can then also include the opening of the shutter during the desorption operation so as to send the secondary flow loaded with molecules to be detected towards the fluorescent material.
- the sensor according to the invention comprises a filter comprising a molecularly imprinted polymer prepared from the molecule to be detected carried by a support.
- the support may be constituted either by a functionalized membrane or by a set of functionalized microbeads.
- MIPs molecular imprinted polymers
- MIPs Like biological receptors, MIPs benefit from a high affinity and good selectivity for given molecules.
- a priori we can design MIPs in the image of any molecule or family of functional molecules ("molecular mecano"): thus, we can consider the synthesis of "custom" MIPs and more particularly for target molecules for which there is no biological equivalent.
- MIPs Due to their highly cross-linked chemical structure, MIPs exhibit very good thermal and chemical stability. They also have the advantage of being synthesized from low-cost reagents. MIPs can be of different types: organic, organic-inorganic hybrid or inorganic. As summarized in the diagram illustrated in FIG. 1 and described in more detail below, the molecularly imprinted polymer (MIP) is obtained by polymerization, using an initiator, and in the presence of a crosslinking agent d one or more types of polyfunctional monomers (mf) in the presence of a molecule called template (mg) which can be either directly the molecule to be detected, or a steric and chemical analog.
- mf polyfunctional monomers
- the template molecule develops interactions with one or more functional monomers in a pore-forming solvent.
- a crosslinking agent and a polymerization initiator leads to the formation of a synthetic matrix containing the recognition sites specifically built around the template molecule.
- dite dite so-called “extraction” step the template molecule is eliminated using an adequate solvent: a polymer matrix is finally obtained having cavities called imprints, the geometric and chemical configuration of which is perfectly adapted the fixation of molecules of interest.
- the MIP may be a hybrid gel obtained from a mixture of silicon alkoxides such as tetramethoxysilane and methylthmethoxysilane, some of which may be functionalized by organic groups, for example the following alkoxide:
- the hybrid MIP gel can then be obtained by reaction of these monomers by hydrolysis and polycondensation in the presence of water and ethanol (an acidic or basic catalyst can also be added) and in the presence of the molecule said to be printed (in particular, 2,4 DNT, a by-product of the manufacture of TNT with a higher vapor pressure than TNT).
- the chemical sensor according to the invention thus has an upstream part capable of selectively filtering a type of molecules and a downstream part comprising the fluorescent material and thereby sites of formation of complexes capable of creating variations in fluorescence representative of the presence or even the concentration of said molecules in the environment in which the sensor will have been placed.
- the transfer process takes place in four stages: 1) Absorption of a photon of Eo energy by the host 2) Relaxation of the environment of a magnitude such that the energy available for a radiative transition of the host is E ⁇ ⁇ E 0 3) Transfer of the energy Ei to the doping complex / extinction site 4) Return to the ground state by a non-radiative process, which explains the decrease in the fluorescence intensity.
- FIG. 2 illustrates this example:
- a pump P1 supplies the sensor with an external flow F1 of ambient air containing molecules to be detected.
- an upstream chamber is thus formed by closing the shutter Op, so as to isolate the filter from the downstream detection part of the sensor, formed at the level of the fluorescent material.
- an inert gas source typically nitrogen
- a flow F2 which desorbs the molecularly imprinted material and makes it possible to generate a charged inert flow molecules to be detected which are sent to the downstream part of the sensor by opening the shutter Op.
- an inert gas makes it possible to limit the photochemical degradation of the fluorescent polymer.
- An opening 01 is provided to release outside the sensor the inert gas charged with other impurities than the molecules which it is specifically sought to detect. The flow F2 loaded with molecules to be detected is transported to the substrates covered with fluorescent material.
- the latter can typically be deposited on the surface of two substrates (S1, S2) oriented parallel to the direction of the flow F2, so as to optimize the exchange surface between said flow and the sites capable of generating charge transfer complexes within the fluorescent polymer.
- a second opening 02 is also provided in the downstream part of the sensor to allow the evacuation of the flow F2.
- the measurement means comprise a light source SL of laser type or laser diode which can typically emit around 450 nm for the detection of DNT molecules with the fluorescent polymers described above, which irradiates all of the substrates carrying the fluorescent polymer .
- a PhotoMultiplier or CCD type photodetector is placed perpendicular to the light source so as to collect part of the radiation scattered by the polymer charged with molecules to be detected without collecting incident light directly emitted by the source.
- the photodetector can detect wavelengths centered on 530 nm (representative of the energy radiations E1 explained above)
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0401395A FR2866429B1 (fr) | 2004-02-12 | 2004-02-12 | Capteur chimique tandem hautement selectif et procede de detection utilisant ce capteur |
PCT/EP2005/050573 WO2005088279A1 (fr) | 2004-02-12 | 2005-02-09 | Capteur chimique tandem hautement selectif et procede de detection utilisant ce capteur |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1714140A1 true EP1714140A1 (de) | 2006-10-25 |
Family
ID=34803314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05716653A Withdrawn EP1714140A1 (de) | 2004-02-12 | 2005-02-09 | Hochselektiver chemischer tandem-sensor und nachweisverfahren damit |
Country Status (4)
Country | Link |
---|---|
US (1) | US20070148696A1 (de) |
EP (1) | EP1714140A1 (de) |
FR (1) | FR2866429B1 (de) |
WO (1) | WO2005088279A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107462561A (zh) * | 2017-09-09 | 2017-12-12 | 华中农业大学 | 烟叶病斑性状荧光动态自动检测装置及方法 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004049805A1 (de) * | 2004-10-12 | 2006-04-13 | Universität Dortmund | Verfahren zur Herstellung von molekulargeprägten Polymeren zur Erkennung von Zielmolekülen |
GB0605427D0 (en) * | 2006-03-17 | 2006-04-26 | Univ Cranfield | Materials For Binding Drugs Of Abuse |
FR2915685A1 (fr) * | 2007-05-02 | 2008-11-07 | Thales Sa | Compose fluorescent a l'etat solide dans l'eau,procede de synthese et utilisation dans des capteurs |
DE102009023636B3 (de) * | 2009-05-26 | 2011-01-27 | BAM Bundesanstalt für Materialforschung und -prüfung | Filtereinheit und Gassensor |
CN106645057B (zh) * | 2016-11-17 | 2019-02-26 | 云南民族大学 | 一种卷烟烟气镉形态的测定方法 |
EP3889599A1 (de) * | 2020-04-01 | 2021-10-06 | Christian-Albrechts-Universität zu Kiel | Analyseverfahren zum nachweis von sprengstoffen auf peroxid-, nitrat- und nitraminbasis |
GB202114557D0 (en) * | 2021-10-12 | 2021-11-24 | Univ Court Univ St Andrews | Apparatus and methods for detection of chemicals using optical sensors |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2665452B1 (fr) * | 1990-07-31 | 1992-10-09 | Thomson Csf | Copolymeres amorphes pour composes photorefractifs utilises dans le traitement du signal optique. |
FR2668158B1 (fr) * | 1990-10-22 | 1994-05-06 | Thomson Csf | Polymere reticulable pour applications en optique non lineaire. |
FR2673190B1 (fr) * | 1991-02-26 | 1994-09-16 | Thomson Csf | Cristaux liquides fluores. |
FR2678613B1 (fr) * | 1991-07-02 | 1993-09-17 | Thomson Csf | Materiaux reticulables thermiquement pour application en optique non lineaire. |
FR2702058B1 (fr) * | 1993-02-23 | 1995-04-07 | Thomson Csf | Procédé d'obtention de matériaux composites à base de polymère et de cristaux liquides avec colorants dichroiques. |
FR2703690B1 (fr) * | 1993-04-06 | 1995-05-12 | Thomson Csf | Matériau électrooptique à base de cristal liquide dispersé dans un polymère, procédé d'élaboration par modification chimique de l'interface et dispositif à base de ce matériau. |
WO2003033575A1 (en) * | 2001-10-16 | 2003-04-24 | The Johns Hopkins University | Polymer based permeable membrane for removal of ions |
-
2004
- 2004-02-12 FR FR0401395A patent/FR2866429B1/fr not_active Expired - Fee Related
-
2005
- 2005-02-09 US US10/589,467 patent/US20070148696A1/en not_active Abandoned
- 2005-02-09 WO PCT/EP2005/050573 patent/WO2005088279A1/fr not_active Application Discontinuation
- 2005-02-09 EP EP05716653A patent/EP1714140A1/de not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO2005088279A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107462561A (zh) * | 2017-09-09 | 2017-12-12 | 华中农业大学 | 烟叶病斑性状荧光动态自动检测装置及方法 |
Also Published As
Publication number | Publication date |
---|---|
US20070148696A1 (en) | 2007-06-28 |
WO2005088279A1 (fr) | 2005-09-22 |
FR2866429A1 (fr) | 2005-08-19 |
FR2866429B1 (fr) | 2006-07-21 |
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