CA2149821C - Process for the silylation of inorganic oxides - Google Patents
Process for the silylation of inorganic oxides Download PDFInfo
- Publication number
- CA2149821C CA2149821C CA002149821A CA2149821A CA2149821C CA 2149821 C CA2149821 C CA 2149821C CA 002149821 A CA002149821 A CA 002149821A CA 2149821 A CA2149821 A CA 2149821A CA 2149821 C CA2149821 C CA 2149821C
- Authority
- CA
- Canada
- Prior art keywords
- silica
- finely divided
- divided inorganic
- inorganic oxides
- silylating agent
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 74
- 230000008569 process Effects 0.000 title claims abstract description 56
- 229910052809 inorganic oxide Inorganic materials 0.000 title claims abstract description 33
- 238000006884 silylation reaction Methods 0.000 title claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 79
- 239000007788 liquid Substances 0.000 claims abstract description 37
- 229910021485 fumed silica Inorganic materials 0.000 claims abstract description 32
- 239000000443 aerosol Substances 0.000 claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 300
- 239000000377 silicon dioxide Substances 0.000 claims description 148
- -1 hydrocarbon radical Chemical class 0.000 claims description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 108
- 239000000203 mixture Substances 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 28
- 238000001179 sorption measurement Methods 0.000 claims description 17
- 125000005372 silanol group Chemical group 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000001282 organosilanes Chemical class 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005375 organosiloxane group Chemical group 0.000 claims description 9
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- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 3
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- 150000002367 halogens Chemical class 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- 150000001412 amines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000000068 chlorophenyl group Chemical group 0.000 description 2
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- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- GYWBHBXGYTYXRG-UHFFFAOYSA-N dichloro-methyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(Cl)Cl GYWBHBXGYTYXRG-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0409—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing Si-atoms
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
- C01B13/14—Methods for preparing oxides or hydroxides in general
- C01B13/145—After-treatment of oxides or hydroxides, e.g. pulverising, drying, decreasing the acidity
-
- 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
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/3081—Treatment with organo-silicon compounds
-
- 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
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/66—Additives characterised by particle size
- C09D7/67—Particle size smaller than 100 nm
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/32—Materials not provided for elsewhere for absorbing liquids to remove pollution, e.g. oil, gasoline, fat
-
- 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
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/22—Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/08—Ingredients agglomerated by treatment with a binding agent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Environmental & Geological Engineering (AREA)
- Public Health (AREA)
- Nanotechnology (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Silicon Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
- Developing Agents For Electrophotography (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4419234.7 | 1994-06-01 | ||
| DE4419234A DE4419234A1 (de) | 1994-06-01 | 1994-06-01 | Verfahren zur Silylierung von anorganischen Oxiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2149821A1 CA2149821A1 (en) | 1995-12-02 |
| CA2149821C true CA2149821C (en) | 2000-05-16 |
Family
ID=6519579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002149821A Expired - Fee Related CA2149821C (en) | 1994-06-01 | 1995-05-19 | Process for the silylation of inorganic oxides |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5686054A (enExample) |
| EP (1) | EP0686676B1 (enExample) |
| JP (1) | JP2918092B2 (enExample) |
| CN (1) | CN1051747C (enExample) |
| AT (1) | ATE169948T1 (enExample) |
| AU (1) | AU669647B2 (enExample) |
| BR (1) | BR9502619A (enExample) |
| CA (1) | CA2149821C (enExample) |
| DE (2) | DE4419234A1 (enExample) |
| ES (1) | ES2121261T3 (enExample) |
| FI (1) | FI116832B (enExample) |
| NO (1) | NO316383B1 (enExample) |
| RU (1) | RU2137712C1 (enExample) |
| TW (1) | TW311904B (enExample) |
| UA (1) | UA43328C2 (enExample) |
Families Citing this family (128)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6191122B1 (en) | 1996-03-29 | 2001-02-20 | DEGUSSA HüLS AKTIENGESELLSCHAFT | Partially hydrophobic precipitated silicas |
| IN191468B (enExample) * | 1996-03-29 | 2003-12-06 | Degussa | |
| DE19742761A1 (de) * | 1997-09-27 | 1999-04-01 | Gerd Dr Rossmy | An ihrer Oberfläche anisotrop verteilte überwiegend hydrophile und überwiegend hydrophobe Domänen aufweisende amphiphile Teilchen oder Moleküle |
| DE19756831A1 (de) | 1997-12-19 | 1999-07-01 | Wacker Chemie Gmbh | Siliciumdioxid, das an seiner Oberfläche teil- oder vollständig silylierte Polykieselsäureketten trägt |
| DE19757210A1 (de) * | 1997-12-22 | 1999-07-01 | Degussa | Hydrophobierte, pyrogen hergestellte Oxide |
| US6159540A (en) * | 1998-01-15 | 2000-12-12 | Cabot Corporation | Polyfunctional organosilane treatment of silica |
| DE69915590T2 (de) * | 1998-01-15 | 2004-08-05 | Cabot Corp., Boston | Verfahren zur herstellung von organisch modifizierter kieselgel |
| WO1999036480A1 (en) * | 1998-01-15 | 1999-07-22 | Cabot Corporation | Method of preparing treated silica |
| US5981131A (en) * | 1998-07-27 | 1999-11-09 | Mitsubishi Chemical America, Inc. | Electrostatic toner composition to enhance copy quality by rejection of ghosting and method of manufacturing same |
| US6383466B1 (en) * | 1998-12-28 | 2002-05-07 | Battelle Memorial Institute | Method of dehydroxylating a hydroxylated material and method of making a mesoporous film |
| US6174926B1 (en) | 1999-01-13 | 2001-01-16 | Cabot Corporation | Method of preparing organically modified silica |
| RU2152967C1 (ru) * | 1999-04-27 | 2000-07-20 | Акционерное общество "Российская инновационная топливно-энергетическая компания" | Способ получения гидрофобного, органофильного кремнезема |
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1994
- 1994-06-01 DE DE4419234A patent/DE4419234A1/de not_active Withdrawn
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1995
- 1995-04-18 TW TW084103815A patent/TW311904B/zh active
- 1995-05-16 US US08/442,452 patent/US5686054A/en not_active Expired - Lifetime
- 1995-05-19 CA CA002149821A patent/CA2149821C/en not_active Expired - Fee Related
- 1995-05-30 AU AU20375/95A patent/AU669647B2/en not_active Ceased
- 1995-05-30 FI FI952622A patent/FI116832B/fi active IP Right Grant
- 1995-05-31 NO NO19952158A patent/NO316383B1/no unknown
- 1995-05-31 RU RU95109149A patent/RU2137712C1/ru not_active IP Right Cessation
- 1995-05-31 JP JP7134467A patent/JP2918092B2/ja not_active Expired - Lifetime
- 1995-05-31 BR BR9502619A patent/BR9502619A/pt not_active IP Right Cessation
- 1995-05-31 UA UA95058463A patent/UA43328C2/uk unknown
- 1995-06-01 EP EP95108429A patent/EP0686676B1/de not_active Expired - Lifetime
- 1995-06-01 AT AT95108429T patent/ATE169948T1/de not_active IP Right Cessation
- 1995-06-01 CN CN95106688A patent/CN1051747C/zh not_active Expired - Lifetime
- 1995-06-01 ES ES95108429T patent/ES2121261T3/es not_active Expired - Lifetime
- 1995-06-01 DE DE59503235T patent/DE59503235D1/de not_active Expired - Lifetime
-
1997
- 1997-06-18 US US08/878,338 patent/US5851715A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU669647B2 (en) | 1996-06-13 |
| EP0686676A1 (de) | 1995-12-13 |
| NO316383B1 (no) | 2004-01-19 |
| CN1051747C (zh) | 2000-04-26 |
| TW311904B (enExample) | 1997-08-01 |
| JPH07330324A (ja) | 1995-12-19 |
| ATE169948T1 (de) | 1998-09-15 |
| US5686054A (en) | 1997-11-11 |
| US5851715A (en) | 1998-12-22 |
| NO952158D0 (no) | 1995-05-31 |
| RU95109149A (ru) | 1997-06-20 |
| EP0686676B1 (de) | 1998-08-19 |
| CN1121044A (zh) | 1996-04-24 |
| JP2918092B2 (ja) | 1999-07-12 |
| FI116832B (fi) | 2006-03-15 |
| DE59503235D1 (de) | 1998-09-24 |
| ES2121261T3 (es) | 1998-11-16 |
| UA43328C2 (uk) | 2001-12-17 |
| FI952622L (fi) | 1995-12-02 |
| CA2149821A1 (en) | 1995-12-02 |
| RU2137712C1 (ru) | 1999-09-20 |
| NO952158L (no) | 1995-12-04 |
| FI952622A0 (fi) | 1995-05-30 |
| AU2037595A (en) | 1996-01-04 |
| DE4419234A1 (de) | 1995-12-07 |
| BR9502619A (pt) | 1996-01-02 |
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