WO1998020080A1 - Pigments revetus d'un agent absorbant le rayonnement ultraviolet - Google Patents
Pigments revetus d'un agent absorbant le rayonnement ultraviolet Download PDFInfo
- Publication number
- WO1998020080A1 WO1998020080A1 PCT/FR1997/001973 FR9701973W WO9820080A1 WO 1998020080 A1 WO1998020080 A1 WO 1998020080A1 FR 9701973 W FR9701973 W FR 9701973W WO 9820080 A1 WO9820080 A1 WO 9820080A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pigment
- filter
- bromide
- pigments
- rubidium
- Prior art date
Links
Classifications
-
- 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
- C09C1/04—Compounds of zinc
- C09C1/043—Zinc oxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
-
- 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
- C09C1/36—Compounds of titanium
-
- 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
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3653—Treatment with inorganic compounds
- C09C1/3661—Coating
-
- 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
- C09C3/06—Treatment with inorganic compounds
- C09C3/063—Coating
-
- 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
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/32—Radiation-absorbing paints
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
Definitions
- the invention relates to pigments coated with an ultraviolet absorbing agent, a process for their preparation, and the paints containing them.
- Space vehicle thermal control uses a variety of techniques, including passive thermal control.
- Passive thermal control is based on the thermo-optical properties of the coatings applied to spacecraft, that is to say:
- This solar absorption coefficient is integrated into the solar spectrum between 0.2 and 2.8 ⁇ m.
- the emissivity e which is a radiation coefficient of the energy depending on the nature of the coatings.
- W e S s T 4 where W: energy exchanged by radiation between the body considered and its environment, S: surface (in cm 2 )
- Passive thermal control coatings can be classified into various categories among which a distinction is made in particular, according to the ratio a s / e: - cold coatings (a s / e ⁇ l) (for example: white paints, metallized plastic films, quartz mirrors, etc.)
- White paints consist of a binder, at least one white pigment and a solvent.
- the most used white pigments are: titanium dioxide (TiC ⁇ ), zinc oxide (ZnO), zinc orthotitanate (Zn 2 Ti0 4 ), 1 Zinc orthostannate (Zn 2 Sn0 4 ), 1 Tin orthotitanate (Sn Ti0 4 ), etc. as well as the mixtures of these pigments.
- thermo-optical properties increase in the solar absorption coefficient: a s
- particulate radiation electro-optical properties
- the white pigments essentially metallic oxides MO *, will lose oxygen to give a product MO ⁇ - y whose thermo-optical properties (a s ) are degraded.
- colored paints consist of a binder, at least one colored pigment and a solvent.
- the colored pigments can be oxides of iron, lead, chromium, etc. or organic pigments, for example diazo compounds, etc.
- the present invention aims to satisfy these needs and others which will appear on reading the description which follows.
- the invention relates to pigments in the form of fine particles having increased stability with respect to solar ultraviolet radiation and particulate radiation (electrons, protons), characterized in that the particles of the pigments are coated with a filter UV absorbing ultraviolet radiation of a wavelength less than 300 nm, but being transparent between the near infrared and the near ultraviolet (ie substantially between 2500 nm and 300 nm) and chosen from
- the amount of UV filter applied to the pigment particles is not very critical. Usually, it will represent 1 to 15% of the weight of the pigment.
- the invention also relates to a process for improving the stability of pigments with respect to ultraviolet or particulate radiation, characterized in that it consists in coating particles of a pigment with an aqueous solution, or in a polar solvent, at least one UV filter, and then drying said pigment particles so as to obtain pigment particles coated with said UV filter, said UV filter absorbing radiation ultraviolet with a wavelength less than 300 nm, but being transparent between the near infrared and the near ultraviolet (ie substantially between 2500 nm and 300 nm) and being chosen from
- a coating method can, for example, consist in dissolving a UV filter in water, or in a suitable polar solvent, in an appropriate concentration, for example which can vary between 2% and 30% by weight, depending on the UV filter. . If necessary, the mixture can be heated for better dissolution. In the resulting solution, the pigment to be treated is added and the mixture is stirred for a few hours to break up the agglomerates of particles which may be present. The pigment is allowed to settle, then it is separated from the solution. After drying, a final grinding can be carried out to break up the agglomerates of particles possibly formed during drying.
- the white pigments coated according to the invention are in particular useful for the manufacture of white paints, in particular of spatial type.
- UV filters which absorb UV below 300 nm and which can be used in the invention are the following:
- KC1 - potassium chloride
- NaCl sodium chloride
- UV filters are soluble in water or polar solvents, such as alcohols, for example methanol, ethanol, isopropanol, etc., polyols, for example glycols, etc.
- the invention further relates to a paint comprising at least one pigment, at least one film-forming binder and, optionally, at least one solvent, characterized in that the pigment is a pigment according to the invention and / or treated with the method of the invention.
- the paints of the invention can be applied in one or more layers on the substrate to be painted, giving paint films with a thickness advantageously between 50 and 200 ⁇ m.
- binders silicone resins or potassium or sodium silicate.
- the treated pigment / binder weight ratio will usually be in the range of 2 to 12, although these values are not narrowly critical.
- a solvent it is possible to use, for information, aromatic hydrocarbons (toluene, xylene, naphtha, etc.), ketones (methyl ethyl ketone, methyl isobutyl ketone, diacetone alcohol, etc.), esters (ethylene glycol acetate, acetate of butylene glycol, etc.) glycol ethers (ethyl glycol, butylglycol, methylene glycol, propylene glycol, etc.), alcohols (ethanol, propanol, butanol, etc.) and water.
- the proportion of solvent will usually be in the range of 0 to 60% by weight based on the total weight of the paint. The value of 0% by weight corresponds to paints without solvent.
- the application of the paint layers containing the treated pigments of the invention to a substrate can be carried out with a paint spray gun, with a brush or by any other known technique.
- the paints of the invention can be applied to all kinds of substrates such as metals, polymeric films or composite materials. If desired, or necessary, a primer coat or any other primer can be applied before applying the paints of the invention.
- the paints of the invention are useful in the aeronautical, automobile or building industries.
- the pigment used was prepared by the following procedure: in 400 ml of the aqueous UV filter solution indicated in the examples, 200 g of the pigment to be treated were added and the mixture was stirred everything for 4 hours. The pigment was allowed to settle, then separated from the solution on a beaker. The pigment was then dried in an oven at 100 ° C for 16 hours. A final regrinding was carried out, if necessary, in the presence of agglomerates of pigment particles.
- the method for testing the paints of the invention is as follows: this accelerated test is intended to assess the resistance to the thermal environment of vehicles, in particular to solar UV radiation space.
- the coating samples to be tested are positioned on a sample holder maintained at 40 ° C for the duration of the test and located in a vacuum chamber whose level is around 5 ⁇ 10 -7 Torr.
- Ultraviolet irradiation is carried out from a 4000 watt short arc Xenon source followed by double interference filtering delivering two ultraviolet bands.
- the irradiation conditions are as follows:
- the values of 1.62 and 10.2 mentioned above correspond to the energy of the integrated solar UV radiation between 200 and 300 nm, and between 300 and 400nm, respectively.
- the irradiations are carried out continuously in the time intervals separating the measurement points carried out at 0.200 and 1000 ehs.
- Particulate irradiations were estimated for different energies in order to best approach the theoretical dose profile calculated for the reference material on the geostationary orbit.
- the dose profiles over a year of geostationary orbit are calculated for two energies in protons and one energy in electrons retained for this stimulation.
- the irradiations were carried out separated by intermediate measurement points by reproducing the dose profile first deep in the material and then progressing towards the surface.
- the total doses were applied in coherence with the equivalent simulation duration for the geostationary orbit represented by 1000 ehs on the North and South faces of a stabilized 3-axis satellite, ie 0.9 years.
- Optical measurements performed in situ consist of measuring spectral reflectance (in the range 250 to 2400 nm) relatively to a reference sample consisting of a thin layer of aluminum evaporated on a glass substrate.
- the system used includes a PERKIN ELMER ⁇ 9 spectrophotometer associated with an integrating sphere with lateral sample that can be placed under vacuum. These relative measurements are supplemented by absolute measurements carried out at the beginning and at the end of the test, in air, using a CARY 2300 spectrometer associated with an integrating sphere with central sample. The correspondence made at the start of the test for each sample between the relative spectrum in situ in air and the absolute spectrum gives the corrective coefficients at each wavelength which are applied to all subsequent relative spectra in situ.
- the value of the solar reflectance calculated from the spectral values taken in the range of 250 to 2400 nanometers is associated with each reflection spectrum.
- the paint of Example 1 contains the untreated zinc orthotitanate pigment.
- This example will serve as a reference and point of comparison with respect to paints produced from pigments according to the invention.
- a white coating is obtained whose thickness after drying is close to 100 micrometers, by applying to a substrate a paint prepared by the following procedure: to 11.50 g of the RTV 121 silicone binder from RHONE-POULENC, 21 g are added toluene, stirred manually, then 69 g of untreated orthotitanate (Zn 2 Ti0) are added to the solution obtained with stirring. After that, the mixture is ground in a 250 ml glass bottle with 100 g of glass beads in a RED DEVIL grinder for 30 minutes. The composition obtained is separated from the beads by sieving.
- the pigment / binder ratio (P / L) is 6.
- a white coating is obtained, the thickness of which after drying is close to 100 micrometers, by applying a paint to a substrate, the composition of which is as follows: - RTV 121 silicone binder (11.5 g) and catalyst 10028 (0.25 g )
- the P / L ratio is 6.
- a white coating is obtained, the thickness of which after drying is close to 100 micrometers, by applying a paint, the composition of which is as follows:
- a white coating is obtained, the thickness of which after drying is close to 100 micrometers, by applying a paint, the composition of which is as follows:
- the P / L ratio is 6.
- a white coating is obtained, the thickness of which after drying is close to 100 micrometers, by applying a paint, the composition of which is as follows:
- the P / L ratio is 6.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19970913245 EP0946653B1 (fr) | 1996-11-05 | 1997-11-04 | Pigments revetus d'un agent absorbant le rayonnement ultraviolet |
AU50569/98A AU716871B2 (en) | 1996-11-05 | 1997-11-04 | Pigments coated with ultraviolet radiation absorbent |
CA 2263528 CA2263528A1 (fr) | 1996-11-05 | 1997-11-04 | Pigments revetus d'un agent absorbant le rayonnement ultraviolet |
JP52109998A JP2001503798A (ja) | 1996-11-05 | 1997-11-04 | 紫外線放射吸収剤で被覆された顔料 |
BR9712864A BR9712864A (pt) | 1996-11-05 | 1997-11-04 | Pigmentos sob forma de partìculas finas que têm uma estabilidade aumentada frente a radiação ultravioleta solar e radiação em partìculas, processo de melhoria da estabilidade de pigmentos, tinta, e utilização da tinta |
DE1997606565 DE69706565T2 (de) | 1996-11-05 | 1997-11-04 | Mit uv-strahlen absorbierenden mittel beschichtete pigmente |
US09/147,641 US6086667A (en) | 1996-11-05 | 1997-11-04 | Pigments coated with ultraviolet radiation absorbent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR96/13452 | 1996-11-05 | ||
FR9613452A FR2755443B1 (fr) | 1996-11-05 | 1996-11-05 | Pigments revetus d'un agent absorbant le rayonnement ultraviolet, procede pour leur preparation et peintures les contenant |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998020080A1 true WO1998020080A1 (fr) | 1998-05-14 |
Family
ID=9497326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1997/001973 WO1998020080A1 (fr) | 1996-11-05 | 1997-11-04 | Pigments revetus d'un agent absorbant le rayonnement ultraviolet |
Country Status (10)
Country | Link |
---|---|
US (1) | US6086667A (fr) |
EP (1) | EP0946653B1 (fr) |
JP (1) | JP2001503798A (fr) |
AU (1) | AU716871B2 (fr) |
BR (1) | BR9712864A (fr) |
CA (1) | CA2263528A1 (fr) |
DE (1) | DE69706565T2 (fr) |
ES (1) | ES2163749T3 (fr) |
FR (1) | FR2755443B1 (fr) |
WO (1) | WO1998020080A1 (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW593569B (en) * | 2000-12-21 | 2004-06-21 | Dainichiseika Color Chem | Near-infrared reflecting composite pigments |
FR2842531B1 (fr) * | 2002-07-18 | 2005-05-20 | Centre Nat Etd Spatiales | Peinture blanche pour controle thermique |
US7455899B2 (en) * | 2003-10-07 | 2008-11-25 | 3M Innovative Properties Company | Non-white construction surface |
US20050142329A1 (en) * | 2003-12-24 | 2005-06-30 | Anderson Mark T. | Energy efficient construction surfaces |
EP1915470A4 (fr) * | 2005-07-29 | 2012-04-04 | Aviza Tech Inc | Appareil de depot destine au traitement de semiconducteurs |
JP5255270B2 (ja) * | 2007-12-27 | 2013-08-07 | 日揮触媒化成株式会社 | コアシェル構造を有する無機酸化物微粒子、該微粒子を含む分散ゾルおよび光学基材用塗布液 |
BR112012009518A2 (pt) * | 2009-10-23 | 2016-05-17 | Homag Holzbearbeitungssysteme | agente de tratamento de superfície contendo uma composição de resina de formação de película bem como cargas e uso do mesmo |
US20130217810A1 (en) * | 2009-10-23 | 2013-08-22 | Homag Holzbearbeitungssysteme Ag | Surface Treating Agent Containing a Film Forming Resin Composition as Well as Fillers, and Use Thereof |
FR2975670B1 (fr) * | 2011-05-26 | 2016-01-15 | Astrium Sas | Piece de remplacement de reflecteur optique solaire pour satellite |
CN102539308B (zh) * | 2011-12-04 | 2013-06-26 | 中国航天科技集团公司第五研究院第五一〇研究所 | 一种白漆热控涂层真空紫外辐射下性能退化预测方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3607338A (en) * | 1968-04-11 | 1971-09-21 | Nasa | Synthesis of zinc titanate pigment and coatings containing the same |
US4460655A (en) * | 1983-04-04 | 1984-07-17 | E. I. Du Pont De Nemours And Company | TiO2 Pigment bearing a coating with fluoride ions and laminate and coating based thereon |
JPH02204326A (ja) * | 1989-01-30 | 1990-08-14 | Teika Corp | ルチル型着色微粒子二酸化チタン組成物及びその製造方法 |
US5296285A (en) * | 1992-05-26 | 1994-03-22 | Mcdonnell Douglas Corporation | High emittance low absorptance coatings |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4460665A (en) * | 1981-12-28 | 1984-07-17 | Ricoh Co., Ltd. | Optical information recording medium |
-
1996
- 1996-11-05 FR FR9613452A patent/FR2755443B1/fr not_active Expired - Fee Related
-
1997
- 1997-11-04 WO PCT/FR1997/001973 patent/WO1998020080A1/fr active IP Right Grant
- 1997-11-04 US US09/147,641 patent/US6086667A/en not_active Expired - Lifetime
- 1997-11-04 AU AU50569/98A patent/AU716871B2/en not_active Ceased
- 1997-11-04 EP EP19970913245 patent/EP0946653B1/fr not_active Expired - Lifetime
- 1997-11-04 BR BR9712864A patent/BR9712864A/pt not_active Application Discontinuation
- 1997-11-04 JP JP52109998A patent/JP2001503798A/ja active Pending
- 1997-11-04 DE DE1997606565 patent/DE69706565T2/de not_active Expired - Lifetime
- 1997-11-04 ES ES97913245T patent/ES2163749T3/es not_active Expired - Lifetime
- 1997-11-04 CA CA 2263528 patent/CA2263528A1/fr not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3607338A (en) * | 1968-04-11 | 1971-09-21 | Nasa | Synthesis of zinc titanate pigment and coatings containing the same |
US4460655A (en) * | 1983-04-04 | 1984-07-17 | E. I. Du Pont De Nemours And Company | TiO2 Pigment bearing a coating with fluoride ions and laminate and coating based thereon |
JPH02204326A (ja) * | 1989-01-30 | 1990-08-14 | Teika Corp | ルチル型着色微粒子二酸化チタン組成物及びその製造方法 |
US5296285A (en) * | 1992-05-26 | 1994-03-22 | Mcdonnell Douglas Corporation | High emittance low absorptance coatings |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, vol. 114, no. 4, 28 January 1991, Columbus, Ohio, US; abstract no. 26686a, page 147; XP002034472 * |
Also Published As
Publication number | Publication date |
---|---|
CA2263528A1 (fr) | 1998-05-14 |
US6086667A (en) | 2000-07-11 |
EP0946653B1 (fr) | 2001-09-05 |
AU716871B2 (en) | 2000-03-09 |
BR9712864A (pt) | 1999-12-07 |
AU5056998A (en) | 1998-05-29 |
EP0946653A1 (fr) | 1999-10-06 |
DE69706565T2 (de) | 2002-07-11 |
ES2163749T3 (es) | 2002-02-01 |
JP2001503798A (ja) | 2001-03-21 |
DE69706565D1 (de) | 2001-10-11 |
FR2755443B1 (fr) | 1999-01-15 |
FR2755443A1 (fr) | 1998-05-07 |
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