EP0456551A1 - Cleaning composition based on 1,1,1,2,2-pentafluoro-3,3-dichloro-propane, and methyl ter butyl ether - Google Patents

Cleaning composition based on 1,1,1,2,2-pentafluoro-3,3-dichloro-propane, and methyl ter butyl ether Download PDF

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Publication number
EP0456551A1
EP0456551A1 EP19910401135 EP91401135A EP0456551A1 EP 0456551 A1 EP0456551 A1 EP 0456551A1 EP 19910401135 EP19910401135 EP 19910401135 EP 91401135 A EP91401135 A EP 91401135A EP 0456551 A1 EP0456551 A1 EP 0456551A1
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Prior art keywords
pentafluoro
butyl ether
dichloro
propane
composition according
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Application number
EP19910401135
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German (de)
French (fr)
Inventor
Daniel Desbiendras
Jean-Jacques Martin
Pascal Michaud
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Arkema France SA
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Elf Atochem SA
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Publication of EP0456551A1 publication Critical patent/EP0456551A1/en
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    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and ethers
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
    • C23G5/02825—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine containing hydrogen
    • C23G5/02841—Propanes
    • C23G5/02851—C2HCl2F5

Definitions

  • the present invention relates to the field of chlorofluorinated hydrocarbons and more particularly relates to a new composition having an azeotrope and usable as an agent for cleaning and degreasing solid surfaces, in particular in defluxing and cold cleaning of printed circuits.
  • 1,1,2-Trichloro-1,2,2-trifluoroethane (known in the art under the designation F113) is widely used in the industry for cleaning and degreasing solid surfaces.
  • F113 1,1,2-Trichloro-1,2,2-trifluoroethane
  • F113 1,1,2-Trichloro-1,2,2-trifluoroethane
  • F113 is most often combined with other organic solvents (for example methanol), preferably in the form of azeotropic or pseudo-azeotropic mixtures which do not demix and which, when used at reflux, have substantially the same composition in the vapor phase as in the liquid phase.
  • organic solvents for example methanol
  • F113 is one of the fully halogenated chlorofluorocarbons that are currently suspected of attacking or degrading stratospheric ozone.
  • the present invention proposes to replace the compositions based on F113 with a new composition based on methyl tert-butyl ether (hereinafter MTBE) and 1,1,1,2,2-pentafluoro. -3,3-dichloro-propane.
  • MTBE methyl tert-butyl ether
  • This latter compound known in the art under the designation 225ca, is practically devoid of destructive effect with respect to ozone.
  • the composition to be used according to the invention comprises from 55 to 80% by weight of 225ca and from 20 to 45% of MTBE.
  • azeotrope whose temperature boiling point is 59.9 ° C. at normal atmospheric pressure (1.013 bar) and the composition according to the invention has a pseudo-azeotropic behavior, that is to say that the composition of the vapor and liquid phases is substantially the same, which is particularly advantageous for the intended applications.
  • the 225ca content is chosen between 62 and 67% by weight and that of MTBE between 38 and 33% by weight.
  • the 225ca / MTBE azeotrope is a negative azeotrope since its boiling point (59.9 ° C) is higher than that of the two constituents (225ca: 51.1 ° C; MTBE: 54 ° C).
  • the composition according to the invention can be advantageously stabilized against hydrolysis and / or free radical attacks likely to occur in the cleaning processes, by adding to it a usual stabilizer such as, for example , nitromethane, propylene oxide or a mixture of these compounds, the proportion of stabilizer can range from 0.01 to 5% relative to the total weight: 225ca + MTBE.
  • a usual stabilizer such as, for example , nitromethane, propylene oxide or a mixture of these compounds
  • composition according to the invention can be used in the same applications and according to the same techniques as the previous compositions based on F113.
  • This azeotrope used for cleaning solder flux or degreasing mechanical parts, gives as good results as compositions based on F113 and methanol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Manufacturing Of Printed Wiring (AREA)

Abstract

In order to replace the cleaning compositions based on 1,1,2-trichloro-1,2,2-trifluoroethane (F113), the invention proposes a composition comprising 55 to 80% by weight of 1,1,1,2,2-pentafluoro- 3,3-dichloropropane (225 ca) and 45 to 20 % by weight of methyl tert-butyl ether. These two compounds form a negative azeotrope (b.p. = 59.9 DEG C at standard pressure). <??>The composition, optionally stabilised, can be used for the cleaning of solid surfaces, in particular for the defluxing of printed circuits and for the degreasing of mechanical components.

Description

La présente invention concerne le domaine des hydrocarbures chlorofluorés et a plus particulièrement pour objet une nouvelle composition présentant un azéotrope et utilisable comme agent de nettoyage et de dégraissage de surfaces solides, en particulier dans le défluxage et le nettoyage à froid de circuits imprimés.The present invention relates to the field of chlorofluorinated hydrocarbons and more particularly relates to a new composition having an azeotrope and usable as an agent for cleaning and degreasing solid surfaces, in particular in defluxing and cold cleaning of printed circuits.

Le 1,1,2-trichloro-1,2,2-trifluoroéthane (connu dans le métier sous la désignation F113) est largement utilisé dans l'industrie pour le nettoyage et le dégraissage des surfaces solides. Outre son application en électronique au nettoyage des flux de soudure pour éliminer le flux décapant qui adhère aux circuits imprimés, on peut mentionner ses applications au dégraissage de pièces métalliques lourdes et au nettoyage de pièces mécaniques de haute qualité et de grande précision comme, par exemple, les gyroscopes et le matériel militaire ou aérospatial. Dans ses diverses applications, le F113 est le plus souvent associé à d'autres solvants organiques (par exemple le méthanol), de préférence sous forme de mélanges azéotropiques ou pseudo-azéotropiques qui ne démixent pas et qui, employés au reflux, ont sensiblement la même composition dans la phase vapeur que dans la phase liquide.1,1,2-Trichloro-1,2,2-trifluoroethane (known in the art under the designation F113) is widely used in the industry for cleaning and degreasing solid surfaces. In addition to its application in electronics to the cleaning of solder fluxes to eliminate the flux flux which adheres to printed circuits, one can mention its applications to the degreasing of heavy metal parts and to the cleaning of high quality and high precision mechanical parts such as, for example , gyroscopes and military or aerospace equipment. In its various applications, F113 is most often combined with other organic solvents (for example methanol), preferably in the form of azeotropic or pseudo-azeotropic mixtures which do not demix and which, when used at reflux, have substantially the same composition in the vapor phase as in the liquid phase.

Cependant, le F113 fait partie des chlorofluorocarbures complètement halogénés qui sont actuellement suspectés d'attaquer ou de dégrader l'ozone stratosphérique.However, F113 is one of the fully halogenated chlorofluorocarbons that are currently suspected of attacking or degrading stratospheric ozone.

Pour contribuer à résoudre ce problème, la présente invention propose de remplacer les compositions à base de F113 par une nouvelle composition à base de méthyl tert-butyl éther (ci-après MTBE) et de 1,1,1,2,2-pentafluoro-3,3-dichloro-propane. Ce dernier composé, connu dans le métier sous la désignation 225ca, est pratiquement dépourvu d'effet destructeur vis-à-vis de l'ozone.To contribute to solving this problem, the present invention proposes to replace the compositions based on F113 with a new composition based on methyl tert-butyl ether (hereinafter MTBE) and 1,1,1,2,2-pentafluoro. -3,3-dichloro-propane. This latter compound, known in the art under the designation 225ca, is practically devoid of destructive effect with respect to ozone.

La composition à utiliser selon l'invention comprend de 55 à 80 % en poids de 225ca et de 20 à 45 % de MTBE. Dans ce domaine, il existe un azéotrope dont la température d'ébullition est de 59,9°C à la pression atmosphérique normale (1,013 bar) et la composition selon l'invention a un comportement pseudo-azéotropique, c'est-à-dire que la composition des phases vapeur et liquide est sensiblement la même, ce qui est particulièrement avantageux pour les applications visées. De préférence, la teneur en 225ca est choisie entre 62 et 67 % en poids et celle de MTBE entre 38 et 33 % en poids.The composition to be used according to the invention comprises from 55 to 80% by weight of 225ca and from 20 to 45% of MTBE. In this area, there is an azeotrope whose temperature boiling point is 59.9 ° C. at normal atmospheric pressure (1.013 bar) and the composition according to the invention has a pseudo-azeotropic behavior, that is to say that the composition of the vapor and liquid phases is substantially the same, which is particularly advantageous for the intended applications. Preferably, the 225ca content is chosen between 62 and 67% by weight and that of MTBE between 38 and 33% by weight.

L'azéotrope 225ca/MTBE est un azéotrope négatif puisque son point d'ébullition (59,9°C) est supérieur à ceux des deux constituants (225ca : 51,1°C ; MTBE : 54°C).The 225ca / MTBE azeotrope is a negative azeotrope since its boiling point (59.9 ° C) is higher than that of the two constituents (225ca: 51.1 ° C; MTBE: 54 ° C).

Comme dans les compositions connues à base de F113, la composition selon l'invention peut être avantageusement stabilisée contre l'hydrolyse et/ou les attaques radicalaires susceptibles de survenir dans les processus de nettoyage, en y ajoutant un stabilisant usuel tel que, par exemple, le nitrométhane, l'oxyde de propylène ou un mélange de ces composés, la proportion de stabilisant pouvant aller de 0,01 à 5 % par rapport au poids total : 225ca + MTBE.As in the known compositions based on F113, the composition according to the invention can be advantageously stabilized against hydrolysis and / or free radical attacks likely to occur in the cleaning processes, by adding to it a usual stabilizer such as, for example , nitromethane, propylene oxide or a mixture of these compounds, the proportion of stabilizer can range from 0.01 to 5% relative to the total weight: 225ca + MTBE.

La composition selon l'invention peut être utilisée dans les mêmes applications et selon les mêmes techniques que les compositions antérieures à base de F113.The composition according to the invention can be used in the same applications and according to the same techniques as the previous compositions based on F113.

Les exemples suivants illustrent l'invention sans la limiter.The following examples illustrate the invention without limiting it.

EXEMPLE 1 :MISE EN EVIDENCE DE L'AZEOTROPE EXAMPLE 1 : DETECTION OF AZEOTROPE

Dans le bouilleur d'une colonne à distiller (30 plateaux), on introduit 100 g de MTBE et 100 g de 225ca. Le mélange est ensuite mis à reflux total pendant une heure pour amener le système à l'équilibre. Au palier de température (59,9°C), on prélève une fraction (environ 50 g) et on l'analyse par chromatographie en phase gazeuse.100 g of MTBE and 100 g of 225ca are introduced into the distiller of a distillation column (30 trays). The mixture is then put under total reflux for one hour to bring the system to equilibrium. At the temperature level (59.9 ° C), a fraction (about 50 g) is taken and analyzed by gas chromatography.

L'examen des résultats, consignés dans le tableau suivant, indique la présence d'un azéotrope 225ca/MTBE.

Figure imgb0001
Examination of the results, recorded in the following table, indicates the presence of a 225ca / MTBE azeotrope.
Figure imgb0001

EXEMPLE 2 :VERIFICATION DE LA COMPOSITION AZEOTROPIQUE EXAMPLE 2 : VERIFICATION OF THE AZEOTROPIC COMPOSITION

Dans le bouilleur d'une colonne à distiller adiabatique (30 plateaux), on introduit 200 g d'un mélange comprenant 64,5 % en poids de 225ca et 35,5 % en poids de MTBE. Le mélange est ensuite porté à reflux pendant une heure pour amener le système à l'équilibre, puis on soutire une fraction d'environ 50 g et on procède à son analyse par chromatographie en phase gazeuse ainsi que celle du pied de distillation. Les résultats consignés dans le tableau suivant montrent la présence d'un azéotrope négatif puisque son point d'ébullition est supérieur à ceux des deux constituants purs : 225ca et MTBE.

Figure imgb0002
200 g of a mixture comprising 64.5% by weight of 225ca and 35.5% by weight of MTBE are introduced into the boiler of an adiabatic distillation column (30 trays). The mixture is then brought to reflux for one hour to bring the system to equilibrium, then a fraction of approximately 50 g is drawn off and its analysis is carried out by gas chromatography as well as that of the distillation bottom. The results recorded in the following table show the presence of a negative azeotrope since its boiling point is higher than those of the two pure constituents: 225ca and MTBE.
Figure imgb0002

Cet azéotrope, employé pour le nettoyage de flux de soudure ou en dégraissage de pièces mécaniques, donne d'aussi bons résultats que les compositions à base de F113 et de méthanol.This azeotrope, used for cleaning solder flux or degreasing mechanical parts, gives as good results as compositions based on F113 and methanol.

EXEMPLE 3 : NETTOYAGE DE FLUX DE SOUDURE EXAMPLE 3 : CLEANING OF WELDING FLOWS

Dans une cuve à ultra-sons Annemasse, on introduit 200 g de la composition azéotropique 225ca/MTBE, puis on porte le mélange à la température d'ébullition.200 g of the azeotropic composition 225ca / MTBE are introduced into an Annemasse ultrasonic tank, then the mixture is brought to the boiling temperature.

Des plaques de verre, enduites de flux de soudure et recuites à l'étuve pendant 30 secondes à 220°C, sont plongées durant 3 minutes dans le liquide à l'ébullition sous ultrasons, puis rincées dans la phase vapeur pendant 3 minutes.Glass plates, coated with solder flux and annealed in an oven for 30 seconds at 220 ° C., are immersed for 3 minutes in the boiling liquid under ultrasound, then rinsed in the vapor phase for 3 minutes.

Après séchage à l'air, une visualisation en lumière rasante revèle l'absence totale de résidu de flux de soudure. On a ainsi obtenu le même résultat qu'avec une composition F113-méthanol (93,7 %-6,3 %).After air drying, viewing in grazing light reveals the total absence of solder flux residue. The same result was thus obtained as with an F113-methanol composition (93.7% -6.3%).

Claims (8)

Composition nettoyante comprenant en poids de 55 à 80 % de 1,1,1,2,2-pentafluoro-3,3-dichloro-propane et de 45 à 20 % de méthyl tert-butyl éther.Cleaning composition comprising by weight from 55 to 80% of 1,1,1,2,2-pentafluoro-3,3-dichloro-propane and from 45 to 20% of methyl tert-butyl ether. Composition selon la revendication 1 contenant en poids de 62 à 67 % de 1,1,1,2,2-pentafluoro-3,3-dichloro-propane et de 38 à 33 % de méthyl tert-butyl éther.Composition according to Claim 1, containing by weight from 62 to 67% of 1,1,1,2,2-pentafluoro-3,3-dichloro-propane and from 38 to 33% of methyl tert-butyl ether. Composition selon la revendication 2 sous forme d'azéotrope bouillant à 59,9°C à la pression normale.Composition according to Claim 2 in the form of an azeotrope boiling at 59.9 ° C at normal pressure. Composition selon l'une des revendications 1 à 3, comprenant en outre au moins un stabilisant.Composition according to one of claims 1 to 3, further comprising at least one stabilizer. Composition selon la revendication 4, dans laquelle le stabilisant est le nitrométhane, l'oxyde de propylène ou un mélange de ces composés.A composition according to claim 4, wherein the stabilizer is nitromethane, propylene oxide or a mixture of these compounds. Composition selon la revendication 4 ou 5, dans laquelle la proportion de stabilisant est de 0,01 à 5 % par rapport au poids total de 1,1,1,2,2-pentafluoro-3,3-dichloro-propane et de méthyl tert-butyl éther.Composition according to Claim 4 or 5, in which the proportion of stabilizer is from 0.01 to 5% relative to the total weight of 1,1,1,2,2-pentafluoro-3,3-dichloropropane and methyl tert-butyl ether. Application d'une composition selon l'une des revendications 1 à 6 au nettoyage des surfaces solides.Application of a composition according to one of claims 1 to 6 for cleaning solid surfaces. Application selon la revendication 7 au défluxage des circuits imprimés et au dégraissage des pièces mécaniques.Application according to claim 7 for defluxing printed circuits and degreasing mechanical parts.
EP19910401135 1990-05-10 1991-04-29 Cleaning composition based on 1,1,1,2,2-pentafluoro-3,3-dichloro-propane, and methyl ter butyl ether Withdrawn EP0456551A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9005807 1990-05-10
FR9005807A FR2661918B1 (en) 1990-05-10 1990-05-10 CLEANING COMPOSITION BASED ON 1,1,1,2,2-PENTAFLUORO-3,3-DICHLORO-PROPANE AND METHYL TERT-BUTYL ETHER.

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EP0456551A1 true EP0456551A1 (en) 1991-11-13

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US (1) US5102563A (en)
EP (1) EP0456551A1 (en)
JP (1) JPH04227799A (en)
CA (1) CA2040980A1 (en)
FR (1) FR2661918B1 (en)

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AU623748B2 (en) * 1989-02-01 1992-05-21 Asahi Glass Company Limited Hydrochlorofluorocarbon azeotropic or azeotropic-like mixture
IE902926A1 (en) * 1989-10-06 1991-04-10 Allied Signal Inc Azeotrope-like compositions of dichloropentafluoropropane¹and 1,2-dichloroethylene
IE66347B1 (en) * 1989-10-06 1995-12-27 Allied Signal Inc Azeotrope-like compositions of dichloropentafluoropropane and a hydrocarbon containing sex carbon atoms
US5494601A (en) * 1993-04-01 1996-02-27 Minnesota Mining And Manufacturing Company Azeotropic compositions
US5578137A (en) * 1993-08-31 1996-11-26 E. I. Du Pont De Nemours And Company Azeotropic or azeotrope-like compositions including 1,1,1,2,3,4,4,5,5,5-decafluoropentane
US6048471A (en) * 1997-07-18 2000-04-11 Richard G. Henry Zero volatile organic compound compositions based upon organic solvents which are negligibly reactive with hydroxyl radical and do not contribute appreciably to the formation of ground based ozone
US6306943B1 (en) 1997-07-18 2001-10-23 Polymer Solvents, Llc Zero volitile organic solvent compositions
EP3297775A1 (en) * 2015-03-24 2018-03-28 Gestalt Sciences Corporation Compositions, devices, systems and methods relating to photo- and thermal- oxidative bleaching of pink-stains

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EP0258079A1 (en) * 1986-07-21 1988-03-02 Elf Atochem S.A. Composition based on methylene chloride and its use in photoresist stripping
EP0347924A1 (en) * 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Use of halogenated hydrocarbon solvents as cleaning agents

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AU623748B2 (en) * 1989-02-01 1992-05-21 Asahi Glass Company Limited Hydrochlorofluorocarbon azeotropic or azeotropic-like mixture
JPH02202998A (en) * 1989-02-02 1990-08-13 Asahi Glass Co Ltd Mixed solvent composition
JP2692233B2 (en) * 1989-02-03 1997-12-17 旭硝子株式会社 Fluorinated hydrocarbon mixed solvent composition
EP0382095B1 (en) * 1989-02-06 1995-05-10 Asahi Glass Company Ltd. Azeotropic or azeotropic-like composition of hydrochlorofluoropropane
US4947881A (en) * 1989-02-24 1990-08-14 Allied-Signal Inc. Method of cleaning using hydrochlorofluorocarbons
US4961869A (en) * 1989-08-03 1990-10-09 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions of 2,3-dichloro-1,1,1,3,3-pentafluoropropane with trans-1,2-dichloroethylene and methanol
IE64912B1 (en) * 1989-10-06 1995-09-20 Allied Signal Inc Azetrope-like compositions of 1,3-dichloro-1,1,2,2,3-pentafluoropropane and 2-methyl-2-propanol
US4970013A (en) * 1989-12-11 1990-11-13 E. I. Dupont De Nemours And Company Binary azeotropic composition of 2,3-dichloro-1,1,1,3-3-pentafluoropropane and methanol

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Publication number Priority date Publication date Assignee Title
FR2128555A1 (en) * 1971-03-03 1972-10-20 Ici Ltd
EP0258079A1 (en) * 1986-07-21 1988-03-02 Elf Atochem S.A. Composition based on methylene chloride and its use in photoresist stripping
EP0347924A1 (en) * 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Use of halogenated hydrocarbon solvents as cleaning agents

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JPH04227799A (en) 1992-08-17
US5102563A (en) 1992-04-07
CA2040980A1 (en) 1991-11-11
FR2661918B1 (en) 1992-07-17
FR2661918A1 (en) 1991-11-15

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