WO1998022648A2 - Verbundwerkstoffe - Google Patents
Verbundwerkstoffe Download PDFInfo
- Publication number
- WO1998022648A2 WO1998022648A2 PCT/EP1997/006370 EP9706370W WO9822648A2 WO 1998022648 A2 WO1998022648 A2 WO 1998022648A2 EP 9706370 W EP9706370 W EP 9706370W WO 9822648 A2 WO9822648 A2 WO 9822648A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nanocomposite
- composite material
- material according
- sol
- substrate
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/006—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character
- C03C17/007—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character containing a dispersed phase, e.g. particles, fibres or flakes, in a continuous phase
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/40—Coatings comprising at least one inhomogeneous layer
- C03C2217/43—Coatings comprising at least one inhomogeneous layer consisting of a dispersed phase in a continuous phase
- C03C2217/44—Coatings comprising at least one inhomogeneous layer consisting of a dispersed phase in a continuous phase characterized by the composition of the continuous phase
- C03C2217/445—Organic continuous phases
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/40—Coatings comprising at least one inhomogeneous layer
- C03C2217/43—Coatings comprising at least one inhomogeneous layer consisting of a dispersed phase in a continuous phase
- C03C2217/46—Coatings comprising at least one inhomogeneous layer consisting of a dispersed phase in a continuous phase characterized by the dispersed phase
- C03C2217/47—Coatings comprising at least one inhomogeneous layer consisting of a dispersed phase in a continuous phase characterized by the dispersed phase consisting of a specific material
- C03C2217/475—Inorganic materials
Definitions
- radicals A are the same or different and represent hydroxyl groups or hydrolytically removable groups, except methoxy, the radicals R are identical or different and represent hydrolytically non-removable groups and x has the value 0, 1, 2 or 3, with at least 50 quantities -% of the silanes x ⁇ 1;
- the substrate is not a glass or mineral fiber and not a plant material.
- The. Substrate can have a wide variety of physical forms and can be, for example, in the form of particles, flakes, fibers, strips, sheets, foils, plates or blocks, have a layered structure or represent a shaped body of any shape.
- the term "particulate" is intended to include powders, flours, granules, chips, chips, beads, pearls, and generally all particles of regular or irregular shape.
- the nanocomposite can also exist in different forms of distribution. For example, the nanocomposite can cover the substrate completely or partially as a continuous coating or coating or be present in a laminate-like manner between a plurality of substrates.
- composite materials of this type are fiber composite materials based on aramids or carbon fibers, metal substrates provided with high-temperature corrosion protection layers, fibers provided with a temperature-resistant impregnation, threads, yarns and semi-finished products such as woven, knitted, crocheted, braided, nonwoven and felt, or molded articles Glass or ceramics, which are connected (laminated) with a metal (e.g. aluminum) foil via the nanocomposite.
- the nanocomposite can also be used as a finish or stiffener, diffusion barrier layer, leach barrier layer, oxidation protection layer, electrical insulation layer or for planarization.
- the nanocomposite can form discontinuous or punctiform contact points between several substrates and e.g. Connect a particulate, flake or fibrous substrate in a matrix-like manner, e.g. is the case with insulation materials.
- inorganic or organic, natural or synthetic materials are suitable as substrate materials for the composite materials according to the invention.
- suitable substrate materials are non-metals such as boron and silicon as well as metals such as iron, chromium, copper, nickel, aluminum, titanium, tin, zinc and silver and corresponding alloys (for example brass, steel, bronze) in the form of powders, fibers, foils, fabrics , Sheets and fittings; Glass materials in the form of powders, flakes, plates or shaped pieces; Ceramic materials in the form of powders, fibers, fabrics, nonwovens, flakes, plates and shaped pieces;
- Sheets and fittings Natural animal fibers and materials such as wool, furs or leather; and minerals such as montmorillonite, bentonite, mica, vermiculite, pearlite, ferrite, spinels, e.g. Magnetite or copper chrome spinel, heavy spar, fluorspar, asbestos, talc, aerogels, sands and clays.
- minerals such as montmorillonite, bentonite, mica, vermiculite, pearlite, ferrite, spinels, e.g. Magnetite or copper chrome spinel, heavy spar, fluorspar, asbestos, talc, aerogels, sands and clays.
- Fibrous substrates are understood to mean both individual fibers, including hollow fibers and whiskers, and corresponding fiber bundles, cords, ropes, twists and yarns and semi-finished products such as fabrics, knitted fabrics, knitted fabrics, braids, textiles, nonwovens, felts, webs and mats. Specific examples of this are carbon fibers, woven fabrics made of synthetic fibers, metal fibers and woven metal.
- the nanocomposite used according to the invention is produced by surface modification of colloidal inorganic particles (a) with one or more silanes (b) optionally in the presence of other additives (c) under the conditions of the sol-gel process.
- sol-gel process Details of the sol-gel process are available from CJ Brinker, GW Scherer: "Sol-Gel Science - The Physics and Chemistry of Sol-Gel-Processing", Academic Press, Boston, San Diego, New York, Sydney (1990) and in DE 1941191, DE 3719339, DE 4020316 and DE 4217432.
- silanes (b) which can be used according to the invention and their hydrolytically removable radicals A and hydrolytically non-removable radicals R are given.
- hydrolyzable groups A are hydrogen, halogen (F, Cl, Br and I, especially Cl and Br), alkoxy (especially C -alkoxy, such as ethoxy, n-propoxy, i-propoxy and butoxy), aryloxy ( in particular C r 6 -.1U_ aryloxy, for example phenoxy), alkaryloxy (for example benzyloxy), acyloxy (in particular C. acyloxy, for example acetoxy and propionyloxy) and alkylcarbonyl (for example acetyl).
- halogen F, Cl, Br and I, especially Cl and Br
- alkoxy especially C -alkoxy, such as ethoxy, n-propoxy, i-propoxy and butoxy
- aryloxy in particular C r 6 -.1U_ aryloxy, for example phenoxy
- alkaryloxy for example benzyloxy
- acyloxy in particular C. acyloxy, for example
- radicals A are amino groups (for example mono- or di-alkyl, aryl and aralkylamine groups with the above-mentioned alkyl, aryl and aralkyl radicals), amide groups (for example benzamido) and aldoxime or ketoxime groups.
- Two or three radicals A together can also form a group complexing the Si atom, as is the case, for example, with Si-polyol complexes which are derived from glycol, glycerol or pyrocatechol.
- Particularly preferred radicals A are C 2 _ 4 alkoxy groups, especially ethoxy. Methoxy groups are less suitable for the purposes of the invention because they have too high reactivity (short processing time of the nanocomposite sol) and can lead to nanocomposites or composite materials with insufficient flexibility.
- the hydrolyzable groups A mentioned can optionally carry one or more customary substituents, e.g. Halogen atoms or alkoxy groups.
- the hydrolytically non-removable groups R are preferably selected from alkyl _ (especially C.. Alkyl, such as methyl, ethyl, propyl and butyl), alkenyl (especially C?. Alkenyl such as vinyl, 1-propenyl, 2-propenyl and butenyl), alkynyl (in particular C_ .alkynyl, such as acetylenyl and propargyl), aryl (in particular C fi _aryl, such as phenyl and naphthyl) and the corresponding alkaryl and Arylalkyl groups. These groups may also optionally have one or more customary substituents, for example halogen, alkoxy, hydroxyl, amino or epoxy groups.
- alkyl, alkenyl and alkynyl groups include the corresponding cyclic groups, e.g. Cyclopropyl, cyclopentyl and cyclohexyl.
- radicals R are optionally substituted C 1 _ 4 alkyl, in particular methyl and ethyl, and optionally substituted C g _ 10 alkyl, especially phenyl.
- the composite materials according to the invention can e.g. be produced from pure methyl riethoxysilane (MTEOS) or from mixtures of MTEOS and tetraethoxysilane (TEOS) as component (b).
- MTEOS methyl riethoxysilane
- TEOS tetraethoxysilane
- silanes with one or more groups R, which are substituted is particularly recommended when the composite material is to be given special properties.
- fluorine atoms eg in the form of substituted aliphatic (especially alkyl) radicals
- a composite material which has water, dirt, dust and oil repellent properties.
- Specific examples of silanes of the general formula (I) are compounds of the following formulas:
- CH Z " CH-Si (OC Z_H t -) _ 6, ⁇ _, HSiClJ_,
- CH 2 CH-Si (OC 2 H 4 OCH 3 ) 3
- CH 2 CH-CH 2 -Si (OC 2 H 5 ) 3
- CH 2 C (CH 3 ) COO-C 3 H 7 -Si- (OC 2 H 5 ) 3
- CH 2 C (CH 3 ) -COO-CH ⁇ Si (OC ⁇ ) 3
- n-CgH ⁇ -CH ⁇ CH ⁇ Si (OC ⁇ ) 3
- silanes can be produced by known methods; see. W. Noll, "Chemistry and Technology of Silicones", Verlag Chemie GmbH, Weinheim / Bergstrasse (1968).
- the proportion of component (b) is usually 20 to 95, preferably 40 to 90 and particularly preferably 70 to 90% by mass, expressed as polysiloxane Formula: R ⁇ SiO (2 _ 0 5 ⁇ ) , which arises during the condensation.
- silanes of the general formula (I) used according to the invention can be used in whole or in part in the form of precondensates, ie compounds which are formed by partial hydrolysis of the silanes of the formula (I), either alone or in a mixture with other hydrolyzable compounds.
- Such oligomers which are preferably soluble in the reaction medium, can be straight-chain or cyclic low-molecular partial condensates (polyorganosiloxanes) with a degree of condensation of, for example, about 2 to 100, in particular 2 to 6.
- the amount of water used for the hydrolysis and condensation of the silanes of the formula (I) is preferably 0.1 to 0.9, and particularly preferably 0.25 to 0.75 mole of water per mole of the hydrolyzable groups present. Particularly good results are often achieved with 0.35 to 0.45 mol of water per mol of the hydrolyzable groups present.
- colloidal inorganic particles (a) are brine and nanoscale dispersible powders (particle size preferably up to 300, in particular up to 100 nm and particularly preferably up to 50 nm) of SiO 2 , TiO ,, ZrO » Al 2 0 3 , Y 2 0 3 , Ce0 2 , Sn0 2 , ZnO, iron oxides or carbon (carbon black and graphite), in particular Si0 2 .
- the proportion of component (a), based on components (a), (b) and (c), is usually 5 to 60, preferably 10 to 40 and particularly preferably 10 to 20% by mass.
- contingent components e.g. Hardening catalysts such as metal salts and metal alkoxides (e.g. aluminum, titanium, zirconium alkoxides), organic binders such as polyvinyl alcohol, polyvinyl acetate, starch, polyethylene glycol and acacia, pigments,
- Hardening catalysts such as metal salts and metal alkoxides (e.g. aluminum, titanium, zirconium alkoxides)
- organic binders such as polyvinyl alcohol, polyvinyl acetate, starch, polyethylene glycol and acacia, pigments,
- Dyes flame-retardant additives
- compounds of glass-forming elements e.g. boric acid, boric acid ester, sodium methylate, potassium acetate, aluminum sec-butoxide, etc.
- corrosion protection agents e.g. aluminum sec-butoxide, etc.
- binders is less preferred according to the invention.
- the hydrolysis and condensation is carried out under sol-gel conditions in the presence of acidic condensation catalysts (for example hydrochloric acid) at a pH of preferably 1 to 2 until a viscous sol is formed.
- acidic condensation catalysts for example hydrochloric acid
- no additional solvent is preferably used.
- alcoholic solvents such as ethanol, or other polar, protic or aprotic solvents, such as tetrahydrofuran,
- Dioxane, dimethylformamide or butyl glycol can be used.
- the nanocomposite sol obtained is preferably subjected to a targeted post-reaction step in which the reaction mixture is heated to temperatures of 40 to 120 ° C. for several hours to several days. Storage for one day at room temperature or heating to 60-80 ° C. for several hours is particularly preferred.
- the viscosity of the sol can also be adjusted to values suitable for the specific application by adding solvents or removing reaction by-products (e.g. alcohols).
- the post-reaction step can also preferably be coupled with a reduction in the proportion of solvent.
- the mass fraction of the nanocomposite in the composite material is preferably 0.1 to 80, in particular 1 to 40 and particularly preferably 1 to 20% by mass.
- the combination of substrate and nanocomposite or nanocomposite sol takes place after an at least initial hydrolysis of component (b) and in any case before the final one
- the nanocomposite sol is preferably activated by adding a further amount of water before it is brought into contact with the substrate.
- the contacting can take place in any manner known to the person skilled in the art and considered useful for the given case, for example by simply mixing the substrate and Nanocomposite sol, dipping, spraying, knife coating, spraying, spinning, pouring, painting, brushing, etc. into or with the nanocomposite sol.
- the final hardening can be preceded by a drying step at room temperature or slightly elevated temperature (e.g. up to approx. 50 ° C).
- the actual hardening or pre-hardening can be carried out at room temperature, but is preferably carried out by heat treatment at temperatures above 50 ° C., preferably above 100 ° C. and particularly preferably at 150 ° C. or above.
- the maximum curing temperature depends, among other things. from
- Melting point or the temperature resistance of the substrate is usually 250 to 300 ° C. In the case of metallic or mineral substrates, however, significantly higher curing temperatures are also possible, for example 400 to 500 ° C. and above.
- the curing can optionally be carried out in a protective gas atmosphere (eg N 2 , argon), in particular if the substrate is sensitive to oxidation. Usual curing times are in the range of minutes to hours, for example 2 to 30 minutes.
- UV-VIS photochemical curing
- electron beam curing rapid annealing
- curing with IR and laser beams curing with IR and laser beams.
- the composite produced can optionally also be subjected to shaping.
- the invention also relates to the use of the above nanocomposite for the coating and / or consolidation of the above substrates.
- the term “consolidation” is intended to include all measures that are suitable for providing the substrate in solidified or compacted form, and thus includes e.g. impregnation of the substrate with nanocomposite, incorporation of the substrate into a matrix of nanocomposite, or bonding or connection of substrates or substrate parts with nanocomposite.
- Coating is understood to mean, in particular, a partial or complete coating of a substrate with a nanocomposite to make this substrate or parts of it special
- the silica sol used therein is an aqueous silica sol from BAYER ("Levasil 300/30") with a solids content of 30% by mass and a particle size of 7 to 10 nm.
- BAYER Levasil 300/30
- MTEOS methyltriethoxysilane
- TEOS tetraethoxysilane
- PTEOS phenyltriethoxysilane.
- ETEOS ethyl triethoxysilane
- EXAMPLE 1 184 ml of MTEOS and 51.4 ml of TEOS are mixed and half of this mixture is stirred vigorously with 62.8 ml of silica sol and 1.71 ml of concentrated (37%) hydrochloric acid. After 5 minutes the second half of the alkoxide mixture is added to the mixture, after which stirring is continued for 5 minutes. The resulting sol is then subjected to a post-reaction step (standing for 15 minutes at room temperature). The sol content of the sol is 327 g / 1.
- the resulting sol is used to impregnate carbon fiber fabrics by padding and then cure them in several layers in a hot press for 20 minutes at 140 ° C under a pressure of 100 kN.
- a solid, elastic carbon fiber composite material is obtained, which is also temperature-stable due to the inorganic binder.
- a 10 x 1 cm strip of this material can be heated with two Bunsen burners for more than 30 minutes without the carbon fibers burning up. In comparison, an epoxy-bonded fabric strip burns when exposed to flame and tears off after 10 minutes.
- EXAMPLE 4 A binder is prepared in accordance with Example 1 by mixing 670 ml of MTEOS and 186 ml of TEOS and dividing in a ratio of 1: 1. Half of the mixture is stirred intensively with 192 g of silica sol (SNOWTEX 50 from Nissan Chemicals) and 4.4 g of concentrated hydrochloric acid are added. After 5 minutes, the second half of the silane mixture is added.
- silica sol SNOWTEX 50 from Nissan Chemicals
- the nanocomposite sol is mixed intensively with 10% by volume of water and stirred for a further 5 minutes. Then soot is mixed in an amount such that the binder accounts for 20% of the solids content.
- the mass is placed in a heated pressing tool (4 cm diameter) and cured for 30 minutes at 140 ° C. under a pressure of 20 kN.
- EXAMPLE 5 Aramid fabrics are impregnated with padding from example 4 and then cured in several layers in a hot press for 20 minutes at 140 ° C. under a pressure of 100 kN.
- EXAMPLE 6 803 ml of MTEOS and 223 ml of TEOS are mixed and separated in a 1: 1 ratio. Half of the silane mixture is stirred vigorously with 165 g of ZrO 2 sol (NZS-30A from Nissan Chemicals) and 4.4 g of concentrated hydrochloric acid and mixed with the second half of the silane mixture after 5 minutes.
- ZrO 2 sol NZS-30A from Nissan Chemicals
- the binder After a post-reaction phase of 12 hours, the binder is mixed intensively with 10% by volume of water and stirred for a further 5 minutes. Boron nitride with an average grain size of 1 ⁇ m is added to the resulting mixture in such an amount that 85% of the total mass consists of boron nitride. The resulting mass is spread on a glass plate with a thickness of approx. 0.5 mm. After drying for 12 hours at room temperature, the layer is removed and sintered at 500 ° C. as a free-standing shaped body. A solid molded body is obtained.
- EXAMPLE 9 A cleaned aluminum sheet is coated as described in Example 8 and, after drying, is kept in air at a temperature of 500 ° C. for 1 hour. This gives a glass-like layer with a thickness of 3 ⁇ m. The sheet coated in this way shows no gas evolution in concentrated hydrochloric acid, while an uncoated sheet dissolves with strong gas evolution.
- EXAMPLE 10 A cleaned stainless steel sheet (1.4301) is dip-coated (primer) with a mixture of 2.5 ml sodium water glass (37/40) and 47.5 ml water and dried at 80 ° C. The stainless steel sheet is then coated as described in Example 8 and, after drying, at a heating rate of 1 K / min. Heated in air at 550 ° C for 1 hour. The stainless steel sheet coated in this way can be subjected to thermal loads in air up to a temperature of 500 ° C. without the sheet becoming discolored.
- Untreated rock wool is sprayed with the standard binder A (solids content: 35% by mass) with a spray gun and constantly swirled in a drum mixer. Binder proportions of 3 to 12% by mass are used. After spraying at 150 ° C., the samples are pressed in a heating press at a pressure of 0.5 t and a heating time of 20 minutes and a cooling time of 20 minutes. Stable moldings are obtained.
- EXAMPLE 13 Preparation of bonded perlite insulation boards
- EXAMPLE 14 Production of high-temperature aramid fiber composites
- Aramid high-modulus fiber fabric Du Pont, Kevlar, basis weight 110 g / cm, washed, twill weave
- the layers are pressed together in the liquid sol.
- the interconnected fabric layers are dried in the binder matrix for 12 hours at room temperature.
- the composite is then compacted at 70 ° C. for 6 hours and at 130 ° C. for 4 hours.
- This process can be used to produce high-temperature aramid fiber composites with several layers. Compared to aramid fiber composites bonded with epoxy resin, the composites are characterized by increased temperature resistance.
- EXAMPLE 16 Preparation of High Temperature Keramide Fiber Composites Silicon carbide fibers ("Nicalon” from Nippon Carbon) are drawn through a suspension with the standard binder C. After drying, the coated fibers are laid into fiber bundles or unidirectional or multidirectional laminates and dried for 12 hours at room temperature. The composites are then compacted for 6 h at 60 ° C and 12 h at 130 ° C. High-temperature silicon carbide composites can be produced using this process.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Composite Materials (AREA)
- Geochemistry & Mineralogy (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Mold Materials And Core Materials (AREA)
- Laminated Bodies (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Glass Melting And Manufacturing (AREA)
- Surface Treatment Of Glass (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Braking Arrangements (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Cereal-Derived Products (AREA)
- Audible-Bandwidth Dynamoelectric Transducers Other Than Pickups (AREA)
- Storage Of Fruits Or Vegetables (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Glass Compositions (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE59713059T DE59713059D1 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe |
EP19970951901 EP0950039B1 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe |
AT97951901T ATE504553T1 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe |
US09/297,571 US6287639B1 (en) | 1996-11-15 | 1997-11-14 | Composite materials |
AU55524/98A AU5552498A (en) | 1996-11-15 | 1997-11-14 | Composite materials |
JP52318798A JP4003810B2 (ja) | 1996-11-15 | 1997-11-14 | 複合物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1996147368 DE19647368A1 (de) | 1996-11-15 | 1996-11-15 | Verbundwerkstoffe |
DE19647368.3 | 1996-11-15 |
Publications (2)
Publication Number | Publication Date |
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WO1998022648A2 true WO1998022648A2 (de) | 1998-05-28 |
WO1998022648A3 WO1998022648A3 (de) | 1998-08-13 |
Family
ID=7811826
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/006373 WO1998022241A2 (de) | 1996-11-15 | 1997-11-14 | Giessereibindemittel |
PCT/EP1997/006370 WO1998022648A2 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe |
PCT/EP1997/006372 WO1998022536A2 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe auf basis von pflanzenmaterialien |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/006373 WO1998022241A2 (de) | 1996-11-15 | 1997-11-14 | Giessereibindemittel |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1997/006372 WO1998022536A2 (de) | 1996-11-15 | 1997-11-14 | Verbundwerkstoffe auf basis von pflanzenmaterialien |
Country Status (14)
Country | Link |
---|---|
US (3) | US6287639B1 (de) |
EP (3) | EP0946313B1 (de) |
JP (4) | JP2001508361A (de) |
CN (1) | CN1236339A (de) |
AT (3) | ATE200235T1 (de) |
AU (3) | AU5482598A (de) |
BR (2) | BR9712956A (de) |
CA (1) | CA2271310A1 (de) |
DE (4) | DE19647368A1 (de) |
ES (3) | ES2155707T3 (de) |
ID (1) | ID18721A (de) |
PL (1) | PL333455A1 (de) |
PT (2) | PT946313E (de) |
WO (3) | WO1998022241A2 (de) |
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US6447577B1 (en) | 2001-02-23 | 2002-09-10 | Intevep, S. A. | Method for removing H2S and CO2 from crude and gas streams |
US6554070B2 (en) | 2001-03-16 | 2003-04-29 | Intevep, S.A. | Composition and method for sealing an annular space between a well bore and a casing |
US6579572B2 (en) | 2001-08-13 | 2003-06-17 | Intevep, S.A. | Water-based system for altering wettability of porous media |
US6579832B2 (en) | 2001-03-02 | 2003-06-17 | Intevep S.A. | Method for treating drilling fluid using nanoparticles |
US6607036B2 (en) | 2001-03-01 | 2003-08-19 | Intevep, S.A. | Method for heating subterranean formation, particularly for heating reservoir fluids in near well bore zone |
WO2008098567A2 (de) * | 2007-02-15 | 2008-08-21 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gesellschaft Mit Beschränkter Haftung | Verfahren zum übertragen von oberflächenstrukturierungen, wie interferenzschichten, hologrammen und anderen hochbrechenden optischen mikrostrukturen |
DE102007008073A1 (de) | 2007-02-15 | 2008-08-21 | Leibniz-Institut für Neue Materialien gem. GmbH | Verfahren zum Übertragen von Oberflächenstrukturierungen, wie Interferenzschichten, Hologrammen und anderen hochbrechenden optischen Mikrostrukturen |
Families Citing this family (131)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19647368A1 (de) * | 1996-11-15 | 1998-05-20 | Inst Neue Mat Gemein Gmbh | Verbundwerkstoffe |
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- 1997-11-14 DE DE59703003T patent/DE59703003D1/de not_active Expired - Lifetime
- 1997-11-14 PT PT97951902T patent/PT946313E/pt unknown
- 1997-11-14 DE DE59703318T patent/DE59703318D1/de not_active Expired - Lifetime
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US6447577B1 (en) | 2001-02-23 | 2002-09-10 | Intevep, S. A. | Method for removing H2S and CO2 from crude and gas streams |
US6740141B2 (en) | 2001-02-23 | 2004-05-25 | Intevep, S.A. | Method for removing H2S and CO2 from above ground hydrocarbon streams |
US6607036B2 (en) | 2001-03-01 | 2003-08-19 | Intevep, S.A. | Method for heating subterranean formation, particularly for heating reservoir fluids in near well bore zone |
US6579832B2 (en) | 2001-03-02 | 2003-06-17 | Intevep S.A. | Method for treating drilling fluid using nanoparticles |
US6554070B2 (en) | 2001-03-16 | 2003-04-29 | Intevep, S.A. | Composition and method for sealing an annular space between a well bore and a casing |
US6579572B2 (en) | 2001-08-13 | 2003-06-17 | Intevep, S.A. | Water-based system for altering wettability of porous media |
WO2008098567A2 (de) * | 2007-02-15 | 2008-08-21 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gesellschaft Mit Beschränkter Haftung | Verfahren zum übertragen von oberflächenstrukturierungen, wie interferenzschichten, hologrammen und anderen hochbrechenden optischen mikrostrukturen |
DE102007008073A1 (de) | 2007-02-15 | 2008-08-21 | Leibniz-Institut für Neue Materialien gem. GmbH | Verfahren zum Übertragen von Oberflächenstrukturierungen, wie Interferenzschichten, Hologrammen und anderen hochbrechenden optischen Mikrostrukturen |
WO2008098567A3 (de) * | 2007-02-15 | 2009-07-09 | Leibniz Inst Neue Materialien | Verfahren zum übertragen von oberflächenstrukturierungen, wie interferenzschichten, hologrammen und anderen hochbrechenden optischen mikrostrukturen |
US9507320B2 (en) | 2007-02-15 | 2016-11-29 | Leibniz-Institut Fuer Neue Materialien Gemeinnuetzige Gesellschaft Mit Beschraenkter Haftung | Method for transferring surface textures, such as interference layers, holograms and other highly refractive optical microstructures |
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