EP0445438B1 - Azeotropartiges Lösemittelgemisch und Verfahren zur Reinigung von elektronischen Bauteilen mit Hilfe desselben - Google Patents
Azeotropartiges Lösemittelgemisch und Verfahren zur Reinigung von elektronischen Bauteilen mit Hilfe desselben Download PDFInfo
- Publication number
- EP0445438B1 EP0445438B1 EP90125837A EP90125837A EP0445438B1 EP 0445438 B1 EP0445438 B1 EP 0445438B1 EP 90125837 A EP90125837 A EP 90125837A EP 90125837 A EP90125837 A EP 90125837A EP 0445438 B1 EP0445438 B1 EP 0445438B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- azeotrope
- weight
- mixture
- methanol
- electronic components
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 20
- 238000004140 cleaning Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000002904 solvent Substances 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 230000004907 flux Effects 0.000 claims description 7
- 238000005476 soldering Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C11D7/5081—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
-
- 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
- C23G5/02803—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 fluorine
Definitions
- 1,4-dihydroperfluorobutane (CHF 2 -CF 2 -CF 2 -CHF 2 ) forms an azeotrope-like solvent mixture with methanol, which is excellent for cleaning electronic components, in particular soldered circuit boards or printed circuits, especially for removal of soldering flux is suitable.
- the invention relates to an azeotrope-like mixture which contains about 3-5% by weight of methanol and about 95-97% by weight of 1,4-dihydroperfluorobutane.
- the mixture preferably contains 3.2-4.0% by weight of methanol, in particular 3.4-3.6% by weight of methanol, the remainder being 1,4-dihydroperfluorobutane in each case.
- Another object of the invention is a method for cleaning electronic components, in particular soldered circuit boards or printed circuits, which is characterized in that the components are washed with an azeotrope-like mixture containing about 3-5% by weight of methanol and 95-97 Wt .-% 1,4-dihydroperfluorobutane contains.
- a mixture is preferably used which contains 3.2-4.0% by weight of methanol, in particular 3.4-3.6% by weight of methanol, the remainder being essentially 1,4-dihydroperfluorobutane.
- a particularly preferred solvent mixture contains 96.5% by weight of 1,4-dihydroperfluorobutane and 3.5% by weight of methanol and has a boiling point of 40.5 ° C. at 1 bar.
- the composition of the vapor is identical or essentially identical to the composition of the liquid, ie the composition of the mixture does not change, or does not change significantly, during evaporation.
- the solvent mixture according to the invention has the further advantage that it contains no chlorine and thus does not cause any damage to the ozone layer. Besides, it is not flammable and can be used in the usual ultrasonic, immersion and brush washing systems.
- a glass fiber-reinforced base material for printed circuit boards based on polyester was coated with a commercially available soldering flux (Zeva C20-200 from Zevatron, main component rosin, alongside activators) and dried in a drying cabinet at 60 ° C. for 18 hours. The material was then washed with a mixture of 1,4-dihydroperfluorobutane (96.5% by weight) and methanol (3.5% by weight) using ultrasound. The exposure time was 5 seconds, the flux was completely removed.
- a commercially available soldering flux Zeva C20-200 from Zevatron, main component rosin, alongside activators
- Example 2 The procedure was as in Example 1, except that another soldering flux was used (Zeva C 30-300 from Zevatron), which in turn contained rosin as the main constituent in addition to activators.
- the flux was completely removed after an exposure time of 10 seconds.
- the treatment times are between 60 and 90 seconds, depending on the flux.
- ionic residues can be removed more easily with the azeotrope than with the conventional mixtures.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Detergent Compositions (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electric Connection Of Electric Components To Printed Circuits (AREA)
Description
- Es ist Stand der Technik, zum Reinigen von gelöteten Leiterplatten und anderen elektronischen Bauteilen Gemische aus 1,1,2-Trichlor-1,2,2-trifluorethan (R 113) und Alkoholen wie Methanol, Ethanol oder 2-Propanol einzusetzen (GB-PS 1 026 003, GB-PS 1 399 867). Aus US-PS 3 960 746 ist eine azeotropartige Mischung aus R 113, Methanol und Nitromethan für denselben Zweck bekannt. Da jedoch die FCKW im Verdacht stehen, die Ozonschicht zu schädigen, ist es notwendig, auf diese Stoffklasse zu verzichten.
- Für den Bereich der Elektronik-Industrie, insbesondere zum Reinigen von Leiterplatten nach dem Lötvorgang, werden zur Zeit verschiedene Systeme auf wäßriger Basis und auf Basis nichthalogenierter organischer Lösemittel diskutiert. Bei wäßrigen Reinigungsmitteln ist es jedoch schwierig, die richtige Tensid/Komplexbildner-Kombination zu finden. Auch muß das System an die mechanische Behandlung wie Spülen, Bürsten, Dampfstrahl, Ultraschall angepaßt werden. Bei der SMT (Surface Mount Technology)-Technik scheiden wäßrige Reinigungssysteme häufig aus, da sich das Wasser nur schwer wieder entfernen läßt.
- Bei Einsatz nichthalogenierter organischer Lösemittel, wie Benzin, Alkohole, Terpene oder Ester ist aufgrund der Brennbarkeit und der Explosivität dieser Substanzen eine explosionsgeschützte Ausführung der Anlage erforderlich, so daß aus ökonomischen Gründen eine Verwendung in Oberflächenbehandlungsanlagen nur in wenigen Fällen infrage kommt.
- Überraschenderweise wurde nun gefunden, daß 1,4-Dihydroperfluorbutan (CHF2-CF2-CF2-CHF2) mit Methanol ein azeotropartiges Lösungsmittelgemisch bildet, welches hervorragend zur Reinigung von elektronischen Bauteilen, insbesondere gelöteten Leiterplatten oder gedruckten Schaltungen, vor allem zur Entfernung von Lötflußmitteln geeignet ist.
- Ein Gegenstand der Erfindung ist ein azeotropartiges Gemisch, das etwa 3 - 5 Gew.-% Methanol und etwa 95 - 97 Gew.-% 1,4-Dihydroperfluorbutan enthält. Vorzugsweise enthält das Gemisch 3,2 - 4,0 Gew.-% Methanol, insbesondere 3,4 - 3,6 Gew.-% Methanol, wobei der Rest jeweils 1,4-Dihydroperfluorbutan ist. Ein weiterer Gegenstand der Erfindung ist ein Verfahren zur Reinigung von elektronischen Bauteilen, insbesondere gelöteten Leiterplatten oder gedruckten Schaltungen, das dadurch gekennzeichnet ist, daß man die Bauteile mit einem azeotropartigen Gemisch wäscht, das etwa 3 - 5 Gew.-% Methanol und 95 - 97 Gew.-% 1,4-Dihydroperfluorbutan enthält. Vorzugsweise verwendet man ein Gemisch, das 3,2 - 4,0 Gew.-% Methanol, insbesondere 3,4 - 3,6 Gew.-% Methanol enthält, wobei der Rest jeweils im wesentlichen 1,4-Dihydroperfluorbutan ist.
- Ein besonders bevorzugtes Lösungsmittelgemisch enthält 96,5 Gew.-% 1,4-Dihydroperfluorbutan und 3,5 Gew.-% Methanol und hat einen Siedepunkt bei 1 bar von 40,5°C.
- Bei dem erfindungsgemäßen Gemisch ist die Zusammensetzung des Dampfes identisch oder im wesentlichen identisch mit der Zusammensetzung der Flüssigkeit, d.h. beim Verdampfen ändert sich die Zusammensetzung des Gemisches nicht oder nicht wesentlich. Das erfindungsgemäße Lösemittelgemisch hat den weiteren Vorteil, daß es kein Chlor enthält, und damit keine Ozonschädigung bewirkt. Außerdem ist es nicht brennbar und kann in den üblichen Ultraschall-, Tauch- und Bürstenwaschanlagen eingesetzt werden.
- Ein glasfaserverstärktes Basismaterial für Leiterplatten auf Polyesterbasis wurde mit einem handelsüblichen Lötflußmittel (Zeva C20-200 der Firma Zevatron, Hauptbestandteil Kolophonium, daneben Aktivatoren) bestrichen und 18 Stunden bei 60°C im Trockenschrank getrocknet. Anschließend wurde das Material mit einem Gemisch aus 1,4-Dihydroperfluorbutan (96,5 Gew.-%) und Methanol (3,5 Gew.-%) unter Anwendung von Ultraschall gewaschen. Die Einwirkzeit betrug 5 Sekunden, das Flußmittel wurde vollständig entfernt.
- Man ging vor wie in Beispiel 1, nur daß man ein anderes Lötflußmittel benutzte (Zeva C 30-300 der Firma Zevatron), welches wiederum als Hauptbestandteil Kolophonium neben Aktivatoren enthielt. Nach einer Einwirkzeit von 10 Sekunden war das Flußmittel vollständig entfernt. Bei den herkömmlichen Gemischen aus 1,1,2-Trichlor-1,2,2-trifluorethan mit Methanol, Ethanol oder 2-Propanol betragen die Behandlungszeiten dagegen je nach Flußmittel zwischen 60 und 90 Sekunden. Außerdem lassen sich ionische Rückstände mit dem Azeotrop besser entfernen als mit den herkömmlichen Gemischen.
Claims (6)
- Verfahren zur Reinigung von elektronischen Bauteilen, insbesondere gelöteten Leiterplatten oder gedruckten Schaltungen, dadurch gekennzeichnet, daß man die Bauteile mit einem azeotropartigen Gemisch wäscht, das etwa 3 - 5 Gew.-% Methanol und etwa 95 - 97 Gew.-% 1,4-Dihydroperfluorbutan enthält.
- Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das azeotropartige Gemisch etwa 3,2 - 4,0 Gew.-% Methanol und etwa 96,0 - 96,8 Gew.-% 1,4-Dihydroperfluorbutan enthält.
- Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das azeotropartige Gemisch etwa 3,4 - 3,6 Gew.-% Methanol und 96,4 - 96,6 Gew.-% 1,4-Dihydroperfluorbutan enthält.
- Verfahren zur Entfernung von Lötflußmitteln, gekennzeichnet durch eine Wäsche mit einem azeotropartigen Gemisch, das etwa 3 - 5 Gew.-% Methanol und etwa 95 - 97 Gew.-% 1,4-Dihydroperfluorbutan enthält.
- Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß das azeotropartige Gemisch etwa 3,2 - 4,0 Gew.-% Methanol und etwa 96,0 - 96,8 Gew.-% 1,4-Dihydroperfluorbutan enthält.
- Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß das azeotropartige Gemisch etwa 3,4 - 3,6 Gew.-% Methanol und 96,4 - 96,6 Gew.-% 1,4-Dihydroperfluorbutan enthält.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4002120 | 1990-01-25 | ||
| DE4002120A DE4002120A1 (de) | 1990-01-25 | 1990-01-25 | Neues azeotropartiges loesemittelgemisch und verfahren zur reinigung von elektronischen bauteilen mit hilfe desselben |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0445438A1 EP0445438A1 (de) | 1991-09-11 |
| EP0445438B1 true EP0445438B1 (de) | 1996-06-05 |
Family
ID=6398744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90125837A Expired - Lifetime EP0445438B1 (de) | 1990-01-25 | 1990-12-31 | Azeotropartiges Lösemittelgemisch und Verfahren zur Reinigung von elektronischen Bauteilen mit Hilfe desselben |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5073291A (de) |
| EP (1) | EP0445438B1 (de) |
| JP (1) | JP2812369B2 (de) |
| DE (2) | DE4002120A1 (de) |
| DK (1) | DK0445438T3 (de) |
| ES (1) | ES2088953T3 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5531916A (en) * | 1990-10-03 | 1996-07-02 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon cleaning compositions |
| FR2676067B1 (fr) * | 1991-05-02 | 1993-07-23 | Atochem | Composition a base de 1,1,1,3,3-pentafluorobutane et de methanol, pour le nettoyage et/ou le sechage de surfaces solides. |
| FR2676066B1 (fr) * | 1991-05-02 | 1993-07-23 | Atochem | Composition a base de 1,1-dichloro-1-fluoroethane, de 1,1,1,3,3-pentafluorobutane et de methanol, pour le nettoyage et/ou le sechage de surfaces solides. |
| EP0519432A3 (en) * | 1991-06-21 | 1993-05-05 | Hoechst Aktiengesellschaft | Azeotrope-like mixture of 2-propanol and 1h-perfluorohexane |
| EP0519431B1 (de) * | 1991-06-21 | 1997-04-16 | SOLVAY (Société Anonyme) | Azeotropartiges Gemisch aus Methanol und 1H-Perfluorhexan |
| US5219488A (en) * | 1992-03-16 | 1993-06-15 | Allied-Signal Inc. | Azeotrope-like compositions of 2-trifluoromethyl-1,1,1,2-tetrafluorobutane and ethanol or isopropanol |
| US5221493A (en) * | 1991-10-18 | 1993-06-22 | E. I. Du Pont De Nemours And Company | Azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and alcohols or ketones |
| EP0610507B1 (de) * | 1991-10-31 | 1998-07-01 | Daikin Industries, Ltd. | Lösemittelzusammensetzung zum reinigen und reinigungsmethode |
| US6355113B1 (en) | 1991-12-02 | 2002-03-12 | 3M Innovative Properties Company | Multiple solvent cleaning system |
| US5194170A (en) * | 1992-04-02 | 1993-03-16 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and either tran-1,2-dichloroethylene, cis 1,2-dichloroethylene, or 1-1 dichloroethane |
| US5250208A (en) * | 1992-04-02 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions |
| US5219490A (en) * | 1992-04-27 | 1993-06-15 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1,2,3,3-pentafluoropropane |
| US5696307A (en) * | 1994-01-21 | 1997-12-09 | Alliedsignal Inc. | Hydrofluoroalkanes as cleaning and degreasing solvents |
| FR2740469B1 (fr) * | 1995-10-31 | 1997-12-05 | Atochem Elf Sa | Compositions de nettoyage a base de 1,1,1,2,2,4,4,- heptafluorobutane et d'alcools |
| US5730894A (en) * | 1996-04-16 | 1998-03-24 | E. I. Du Pont De Nemours And Company | 1,1,2,2,3,3,4,4-octafluorobutane azeotropic (like) compositions |
| US5769935A (en) | 1996-11-26 | 1998-06-23 | Alliedsignal Inc. | Use of fluorocarbons as a fusing agent for toners in laser printers |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129954C (de) * | 1964-04-02 | |||
| GB1399867A (en) * | 1971-09-27 | 1975-07-02 | Ici Ltd | Cleaning process |
| GB1430582A (en) * | 1972-01-14 | 1976-03-31 | Haszeldine R N | Preparation of fluorinated organic materials |
| US3960746A (en) * | 1974-07-25 | 1976-06-01 | E. I. Du Pont De Nemours And Company | Azeotrope-like compositions of methanol, nitromethane and trichlorotrifluoroethane |
| US4157979A (en) * | 1978-04-07 | 1979-06-12 | Phillips Petroleum Company | Azeotropic compositions |
| US4810412A (en) * | 1988-04-11 | 1989-03-07 | E. I. Du Pont De Nemours And Company | Azeotropic compositions of 1,1-difluoro-2,2-dichloroethane and methanol or ethanol |
| US4816174A (en) * | 1988-05-03 | 1989-03-28 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane, methanol and nitromethane |
| DE68912325T2 (de) * | 1988-05-03 | 1994-04-28 | Allied Signal Inc | Azeotropähnliche zusammensetzungen von 1,1-dichloro-1-fluoroethan, methanol und nitromethan. |
| US4842764A (en) * | 1988-05-03 | 1989-06-27 | Allied-Signal Inc. | Azeotrope-like compositions of 1,1-dichloro-1-fluoroethane and methanol |
| JPH02221386A (ja) * | 1989-02-23 | 1990-09-04 | Asahi Glass Co Ltd | 塩素化弗素化炭化水素系脱脂洗浄剤 |
-
1990
- 1990-01-25 DE DE4002120A patent/DE4002120A1/de not_active Withdrawn
- 1990-12-31 EP EP90125837A patent/EP0445438B1/de not_active Expired - Lifetime
- 1990-12-31 DK DK90125837.6T patent/DK0445438T3/da active
- 1990-12-31 DE DE59010360T patent/DE59010360D1/de not_active Expired - Fee Related
- 1990-12-31 ES ES90125837T patent/ES2088953T3/es not_active Expired - Lifetime
-
1991
- 1991-01-23 JP JP3006388A patent/JP2812369B2/ja not_active Expired - Lifetime
- 1991-01-23 US US07/644,512 patent/US5073291A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE59010360D1 (de) | 1996-07-11 |
| US5073291A (en) | 1991-12-17 |
| JP2812369B2 (ja) | 1998-10-22 |
| EP0445438A1 (de) | 1991-09-11 |
| ES2088953T3 (es) | 1996-10-01 |
| DK0445438T3 (da) | 1996-11-04 |
| JPH04213397A (ja) | 1992-08-04 |
| DE4002120A1 (de) | 1991-08-01 |
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