EP1920245A1 - Procede de fonctionnalisation successive d un substrat et microstructure obtenue par ce procede - Google Patents
Procede de fonctionnalisation successive d un substrat et microstructure obtenue par ce procedeInfo
- Publication number
- EP1920245A1 EP1920245A1 EP06776577A EP06776577A EP1920245A1 EP 1920245 A1 EP1920245 A1 EP 1920245A1 EP 06776577 A EP06776577 A EP 06776577A EP 06776577 A EP06776577 A EP 06776577A EP 1920245 A1 EP1920245 A1 EP 1920245A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- zone
- chemical
- zones
- substance
- functionalization
- 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- Withdrawn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
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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0046—Sequential or parallel reactions, e.g. for the synthesis of polypeptides or polynucleotides; Apparatus and devices for combinatorial chemistry or for making molecular arrays
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00351—Means for dispensing and evacuation of reagents
- B01J2219/00387—Applications using probes
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00497—Features relating to the solid phase supports
- B01J2219/00527—Sheets
- B01J2219/00529—DNA chips
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00608—DNA chips
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00612—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports the surface being inorganic
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00614—Delimitation of the attachment areas
- B01J2219/00617—Delimitation of the attachment areas by chemical means
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00614—Delimitation of the attachment areas
- B01J2219/00617—Delimitation of the attachment areas by chemical means
- B01J2219/00619—Delimitation of the attachment areas by chemical means using hydrophilic or hydrophobic regions
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00623—Immobilisation or binding
- B01J2219/00626—Covalent
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
- B01J2219/00632—Introduction of reactive groups to the surface
- B01J2219/00637—Introduction of reactive groups to the surface by coating it with another layer
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00603—Making arrays on substantially continuous surfaces
- B01J2219/00659—Two-dimensional arrays
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00718—Type of compounds synthesised
- B01J2219/0072—Organic compounds
- B01J2219/00722—Nucleotides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Definitions
- the invention relates to a method of successively functionalizing a substrate and to the micro structure obtained by this method.
- the word functionalization defines the action of attaching or grafting a chemical molecule onto a support.
- the purpose of this functionalization is to confer specific properties on said support (wettability, adsorption, neutral or charged surface, chemical reactivity for the grafting of chemical or biological molecules.)
- the invention relates to a method of successive functionalization of a substrate, at the surface of which are at least two zones made of different materials, with at least one chemical substance without masking.
- microsystem To confer properties of very specific surfaces on the surface of a microsystem (microstructure) is an important problem in the field of microtechnologies. It is even more important to have these different properties on the same support consisting of different areas. Each zone can thus lead to different properties.
- zone 2 functionalization of zone 1, unmasking of zone 2, possibly masking of zone 1, functionalization of zone 2, - if zone 1 has been masked, unmasking of this zone
- Surface functionalization is often provided by the reaction of an organic silane on an oxide layer, for example SiO 2 . Numerous examples will be noted concerning the production of surfaces comprising hydrophilic and hydrophobic zones made according to the diagram indicated in FIG. 1.
- the application of the organic layer may be carried out for example by dipping in the liquid phase (see “Nanoliter liquid metering in microchannels using hydrophobic patterns “Anal Chemicals 2000, 72, 4100-4109), in the gaseous phase, by embossing (see” Chemical nano-patterning using hot embossing lithography “, Microelectronics Engineering 2002, 61-62, 423-428) by spin coating (see “Automatic transportation of a droplet on a wettability gradient surface", 7th International Conference on Miniaturized Chemical and Biochemical Analysis Systems, October 5-9, 2003, Sqaw Valley, CA (USA)).
- zone 1 functionalization to be preserved
- degradation of the chemical functionalization layer on zone 2 for example by O 2 plasma
- functionalization of zone 2 unmasking of zone 1 .
- WO-A-02/16023 describes for example these two types of approach.
- US 2005/0014151 discloses a method named SMAP (selective molecular assembly patterning technique) that uses three variants to selectively functionalize surface areas of a substrate:
- SMAP selective molecular assembly patterning technique
- One variant uses monolayers of alkane phosphates which form self-assembled monolayers (self-assembled monolayers).
- the other variant uses polyionic polymers due to their electrostatic nature and hydrophobic polymers.
- the chemical functionalization in this document is therefore only by selective adsorption on the surface of an area to be functionalized by molecules.
- the masking of the zones is carried out by a polymer.
- a polymer In general, the simultaneous presence of sub-molecular substances [instead of "chemistry"] (in particular solvents) and of this polymer (photosensitive or non-photosensitive) leads to compatibility problems.
- the resin may optionally be replaced by a deposit metal, but it is a part of a heavier technology (metal deposition, resin deposit, photolithography to open reactive zones, etching), on the other hand the metals are also attacked by strong acids.
- the objective of the present invention is therefore to avoid the problems of the prior art and to provide a suitable method for the functionalization of the microstructures.
- the present invention therefore relates to a method of successively functionalizing a substrate, on the surface of which there are at least two zones made of different materials, with at least one chemical substance, characterized in that the functionalization is carried out without masking and in what he understands the steps
- the present invention also relates to a microstructure containing zones which consist of different materials, wherein at least one zone is functionalized by chemical bonding, achievable by a method according to the method of the present invention.
- FIG. 1 illustrates the conventional method of localization (functionalization) according to the state of the art.
- FIG. 2 illustrates another conventional method of localization (functionalization) according to the state of the art.
- Figure 3 illustrates the method according to an exemplary embodiment of the present invention.
- FIG. 1 illustrates the method of functionalization according to the state of the art on a support 3 of a microstructure.
- a zone 2 is masked in a first step 5. Then, the zone 1 is functionalized in a second step 6 and after, the zone 2 is unmasked. If the zone 1 is masked in a step 5, it follows a functionalization step 6 of the zone 2 and unmasking 7 of the zone 1. Alternatively, the zone 2 could functionalised directly after the unmasking of the zone 2.
- FIG. 1 illustrates another method of functionalization according to the technical state. The order of these steps is as follows:
- Figure 3 illustrates the method according to an exemplary embodiment of the present invention.
- the zone 1 is functionalized by reaction forming a covalent bond through the transformation of the substrate with a chemical substance. Some parts of this chemical substance X 1 also react with zone 2. Consequently, zone 2 is treated with a chemical substance Y 1 to clean these zones of the substance X 1 and / or its reaction products, which have deposited on these zones during the functionalization of the first zone, without the functionalized surface of the first zone being damaged.
- zone 2 is activated by chemical activation or physical (step 9) and then functionalized (step 6). A functionalization of a substrate of the different zones is thus obtained by the formation of covalent bonds.
- steps (b1), (b2) and / or (c) could be repeated one or more times, for example using in the steps (a) and (c) chemical substances X different from X 1 and X 2 and in steps (bl) and / or (b2) of different chemicals Y of Y 1 and Y 2.
- step (bl) and / or step (b2) is carried out in acidic or basic medium.
- Preferred X 1 molecules having alkene, alkyne, halogen, diazo, thio, di or tri-coordinated phosphine atom (phosphine, phosphinine), aldehyde, alcohol groups.
- Preferred X 2 molecules having silane, siloxane, pentacoordinated phosphorus atom (phosphate, phosphonate) moieties.
- the conductive or semiconductor materials are selected from those of the group comprising silicon, crystalline or amorphous carbon, optionally doped n or p and metals.
- Preferred metals are gold, silver, copper, nickel, aluminum.
- the preferable materials are silicon, germanium, carbon in crystalline or amorphous form, dope (graphite, carbon nanotubes, mono or polycrystalline diamond.
- Preferable combinations of materials from different areas are gold / oxide, Si / Si oxide, aluminum / Si oxide, Si / Si nitride, gold / Si / Si oxide.
- PDMS poly (dimethylsiloxane)
- acrylic polymers such as PMMA, etc.
- Cleaning and activation steps could therefore be carried out in an acidic or basic medium with chemical substances Y 1 , Y 2 or Y, for example HF at different dilutions and possibly buffered, a mixture H 2 SO 4 / H 2 O 2 in varying proportions, HNO 3 , their mixtures and strong bases such as NaOH, KOH.
- chemical substances Y 1 , Y 2 or Y for example HF at different dilutions and possibly buffered, a mixture H 2 SO 4 / H 2 O 2 in varying proportions, HNO 3 , their mixtures and strong bases such as NaOH, KOH.
- the functionalized zones could be modified by means of chemical bonds or physical treatment.
- the substrate is therefore structured in different areas (different materials). This structuring can be performed by microtechnology techniques (masking, photolithography, etching or deposition, unmasking).
- the zones can be differentiated for example at the hydrophilic level.
- the zones can here derive from a single material, which can subsequently be modified chemically.
- the chemical modification can also be, for example, the transformation in 2 steps of an epoxide function in aldehyde function to graft molecules with amine-type groups.
- an ester function can be converted into an acid function to give hydrophilic surfaces and also reactive with NH 2 functions.
- the method of the present invention further comprises sequential functionalization with at least one chemical substance.
- the functionalization of a first zone could "polluting" also a second zone or subsequent zones by non-specific adsorption of reagents used for this functionalization.
- the method of the present invention could be used for the preparation of chemical and biological sensors, in the context of the production of DNA chips, proteins, sugars, peptides, small organic molecules for therapeutic purposes, and also for the preparation of fluidic microsystems requiring functionalization of their walls.
- the method of the present invention could be used for the preparation of any microelectronic device where it is necessary to impart mechanical or chemical properties to the surfaces of this device.
- This invention makes it possible to functionally differentiate two zones of a structured or non-structured support (glass, polymers, silicon, mineral oxide layers, etc.) without protection of any of the areas during the chemical process.
- the present invention proposes an approach whose main interest is to be able to completely dissociate the technology steps (masking, etching, photolithography, etc.) and chemical functionalization (see FIG. 3).
- the protocol described is an example of the method of the present invention. It integrates:
- zone A the functionalization of zone A, the cleaning and activation of zone B (simultaneously), the functionalization of zone B, the chemical modification of the functions of zone B.
- a drop of liquid deposited on the flat surface of a solid body forms a contact angle at the interface between the liquid and the substrate.
- a drop is a liquid that does not wet and has a contact angle greater than 90 °.
- the measurement of contact angles is a method for characterizing the interaction between a liquid and a solid surface.
- the contact angle and the function of the surface tension of the liquid and the surface free energy of the substrate are also called direction finding (C. J. Van Oz "Medium interfacial force, 1996).
- a non-oxidized silicon surface is regenerated on zone 1 by soaking the substrate in dilute HF (1%) for a short time (a few tens of seconds) in order to limit the consumption of the SiO 2 layer (zone 2).
- the substrate is dried under nitrogen flow and then introduced in reaction with 1-octadecene.
- the reaction takes place under argon at 150 ° C for 12 hours.
- the substrate is then rinsed successively with various solvents (heptane, dichloromethane, acetone, ethanol, water).
- the contact angle measurement indicates that zone A is functionalized (contact angle of 102 ° close to theoretical 105 ° for a perfectly organized surface, Table 1) while zone B is polluted by organic molecules (86 °) .
- the next step cleans this zone B and activates it by creating silanol groups (contact angle of 13 °) without noticeably degrading the zone A (contact angle from 102 to 100 °).
- Zone B is then functionalized with a silane carrying an epoxide function according to one of the methods known in the art.
- the contact angle obtained (66 °) is characteristic of this type of surface. It is obtained by preserving almost completely the surface properties of zone A (passage from 100 to 90 °).
- a solution of oligomer (10 ⁇ M, phosphate buffer) of 20 seas modified by an NH 2 functional reactive function of the aldehyde functions of the surface (5 'NH 2 TT TCG TTT GAT ACC CAA GGA 3') are deposited on this surface at room temperature. using a robot equipped with piezoelectric heads that eject drops of 330 pL.
- a reducing post-treatment is carried out (0.1M NaBH 4 ) and the substrate is then rinsed with 0.2% SDS and with deionized water.
- a complementary target solution 5 'GTC TCC TTG GGT ATC CGA TGT 3'
- This technology thus makes it possible to obtain spots of excellent quality, in particular in terms of size and alignment (conditioned by the design of the underlying inorganic materials) but also in terms of homogeneity within a spot.
- Another example which works in principle as the execution example number 1 uses a substrate whose surface comprises a plurality of zones.
- the plurality of different areas is divided by groups of areas consisting of the same material.
- each zone of the plurality (several tens, or even hundreds) of the zones may consist of a different material.
- the material of the plurality of zones was gold and silicon oxide, i.e., the substrate had two groups of zones each of which consisted of a different material.
- the reagent X 1 is preferably a thiol
- the reagent X 2 is a silane or siloxane.
- fluoric acid (HF) is preferred.
- the reagent X 1 is chosen from alkenes, alkines and halogens.
- the reagent Y is HF or H 2 SO 4 , the reagent X 2 is a thiol, the reagent Y is the fluoric acid HF and the reagent X 3 is a silane and siloxane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0508221A FR2889516B1 (fr) | 2005-08-02 | 2005-08-02 | Procede de fonctionnalisation successive d'un substrat et microstructure obtenue par ce procede |
PCT/EP2006/007665 WO2007014775A1 (fr) | 2005-08-02 | 2006-08-02 | Procede de fonctionnalisation successive d’un substrat et microstructure obtenue par ce procede |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1920245A1 true EP1920245A1 (fr) | 2008-05-14 |
Family
ID=36658670
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06776577A Withdrawn EP1920245A1 (fr) | 2005-08-02 | 2006-08-02 | Procede de fonctionnalisation successive d un substrat et microstructure obtenue par ce procede |
Country Status (5)
Country | Link |
---|---|
US (1) | US20090053481A1 (fr) |
EP (1) | EP1920245A1 (fr) |
JP (1) | JP2009505844A (fr) |
FR (1) | FR2889516B1 (fr) |
WO (1) | WO2007014775A1 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008138934A2 (fr) * | 2007-05-09 | 2008-11-20 | Westfälische Wilhelms-Universität Münster | Procédé pour la fabrication de structures monocouches fonctionnelles imprimées et produits de celui-ci |
CA2761966A1 (fr) * | 2009-05-29 | 2010-12-02 | Georgia Tech Research Corporation | Composants thermochimiques de nanolithographie, systemes et procedes |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0353328A1 (fr) * | 1988-08-03 | 1990-02-07 | Dräger Nederland B.V. | Capteur à trois électrodes pour mesures polarographiques et amperométriques |
US6897073B2 (en) * | 1998-07-14 | 2005-05-24 | Zyomyx, Inc. | Non-specific binding resistant protein arrays and methods for making the same |
WO2001017670A1 (fr) * | 1999-09-09 | 2001-03-15 | Ben-Gurion University Of The Negev | Matrices de sondes et preparation de celles-ci |
US20050014151A1 (en) * | 2001-09-12 | 2005-01-20 | Marcus Textor | Device with chemical surface patterns |
KR20050057353A (ko) * | 2002-09-19 | 2005-06-16 | 코닌클리즈케 필립스 일렉트로닉스 엔.브이. | 스페이서에 의해 서로 이격된 한 쌍의 기판 및 그것의 제조방법, 그것을 포함하는 장치 및 lcd 기판 |
US7399365B2 (en) * | 2003-04-18 | 2008-07-15 | Ekc Technology, Inc. | Aqueous fluoride compositions for cleaning semiconductor devices |
US20050019745A1 (en) * | 2003-07-23 | 2005-01-27 | Eastman Kodak Company | Random array of microspheres |
US7780841B2 (en) * | 2005-02-15 | 2010-08-24 | Hewlett-Packard Development Company. L.P. | E-field induced ion selective molecular deposition onto sensor arrays |
-
2005
- 2005-08-02 FR FR0508221A patent/FR2889516B1/fr not_active Expired - Fee Related
-
2006
- 2006-08-02 WO PCT/EP2006/007665 patent/WO2007014775A1/fr active Application Filing
- 2006-08-02 EP EP06776577A patent/EP1920245A1/fr not_active Withdrawn
- 2006-08-02 JP JP2008524439A patent/JP2009505844A/ja active Pending
- 2006-08-02 US US11/997,477 patent/US20090053481A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2007014775A1 * |
Also Published As
Publication number | Publication date |
---|---|
FR2889516A1 (fr) | 2007-02-09 |
FR2889516B1 (fr) | 2007-10-19 |
WO2007014775A1 (fr) | 2007-02-08 |
JP2009505844A (ja) | 2009-02-12 |
US20090053481A1 (en) | 2009-02-26 |
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