EP0144663B1 - Verwendung von Korrosionsinhibitoren in wässrigen Systemen - Google Patents
Verwendung von Korrosionsinhibitoren in wässrigen Systemen Download PDFInfo
- Publication number
- EP0144663B1 EP0144663B1 EP84112673A EP84112673A EP0144663B1 EP 0144663 B1 EP0144663 B1 EP 0144663B1 EP 84112673 A EP84112673 A EP 84112673A EP 84112673 A EP84112673 A EP 84112673A EP 0144663 B1 EP0144663 B1 EP 0144663B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- corrosion inhibitors
- aqueous systems
- salts
- hydrogen
- alkyl radical
- 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
Links
- 230000007797 corrosion Effects 0.000 title claims abstract description 11
- 238000005260 corrosion Methods 0.000 title claims abstract description 11
- 239000003112 inhibitor Substances 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VBLZXGQFGDIFIP-UHFFFAOYSA-N 2-(benzenesulfonamido)hexanoic acid Chemical compound CCCCC(C(O)=O)NS(=O)(=O)C1=CC=CC=C1 VBLZXGQFGDIFIP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000005068 cooling lubricant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/12—Oxygen-containing compounds
- C23F11/124—Carboxylic acids
- C23F11/126—Aliphatic acids
Definitions
- the invention relates to the use of salts of special aroylcarboxylic acids as corrosion inhibitors in aqueous systems.
- Corrosion protection in aqueous systems is a major problem in technical processes when it affects metals at risk, such as copper, zinc or aluminum.
- the use of corrosion inhibitors, for example in cleaning agents, cooling lubricants, hydraulic fluids or cooling water, has so far often led to a number of application problems. Foam formation, for example, is undesirable.
- the water solubility or the water hardness stability is also important for the usability of the agents.
- the toxicity and degradability of the substances and their storage stability also play an important role.
- alkali metal salts such as sodium or potassium salts
- ammonium salts with organic bases such as ammonia, mono-, di- or trialkanolamines
- organic bases such as ammonia, mono-, di- or trialkanolamines
- diethanolamine has proven to be advantageous.
- the anticorrosive agents according to the invention can moreover be used individually or as a mixture in aqueous solutions, dispersions or emulsions.
- a high level of effectiveness is available even at low concentrations. It has been shown that a sufficient effect is sometimes achieved with 0.5 kg / m 3 .
- Quantities of 0.5 to 10 kg / m 3 , preferably 1 to 10 kg / m 3 are therefore suitable.
- the agents used also have a pronounced lack of foam and have good water hardness stability.
- the aroylcarboxylic acids are prepared by methods known per se. They can be obtained, for example, by Friedel-Crafts acylation of alkylbenzenes with appropriate cyclic anhydrides. The preparation of the aroylcarboxylic acids or their salts is not the subject of the invention.
- test strips Three carefully pretreated and weighed test strips (unalloyed steel, 80 x 15 x 1 mm) were hung in a 1 l vessel containing 800 ml test water, 50 ml buffer solution and a defined amount of the substance to be examined, and added for 3 hours Leave room temperature and 80 revolutions per minute in it.
- the corrosion protection value S was calculated from the weight loss.
- test water used as a corrosive medium was produced in accordance with DIN 51360/2 and. buffered with ammonia / ammonium chloride.
- Table 4 shows the results obtained in comparison with benzenesulfonamidocaproic acid.
- Tables 1 to 3 show which compounds are involved in the products according to formula I designated A to T.
- the specified bases were used to neutralize the aroylcarboxylic acids.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Detergent Compositions (AREA)
Description
- Gegenstand der Erfindung ist die Verwendung von Salzen von speziellen Aroylcarbonsäuren als Korrosionsinhibitoren in wäßrigen Systemen.
- Der Korrosionsschutz in wäßrigen Systemen ist ein wesentliches Problem bei technischen Prozessen, wenn dabei gefährdete Metalle, wie Kupfer, Zink oder Aluminium, betroffen werden. Die Verwendung von Korrosionsinhibitoren, beispielsweise in Reinigungsmitteln, Kühlschmiermitteln, Hydraulikflüssigkeiten oder Kühlwässern, führte bisher oft zu einer Reihe von anwendungstechnischen Problemen. Es ist beispielsweise die Schaumbildung unerwünscht. Die Wasserlöslichkeit oder auch die Wasserhärtestabilität ist für die Brauchbarkeit der Mittel ebenso von Bedeutung. Weiterhin spielt die Toxizität und die Abbaubarkeit der Substanzen sowie ihre Lagerstabilität eine wesentliche Rolle.
- In letzter Zeit sind als Korrosionsinhibitoren bereits langkettige, aliphatische Sulfonamidocarbonsäuren beziehungsweise Arylsulfonamidocarbonsäuren vorgeschlagen worden. Diese Inhibitoren zeigen jedoch nur bei hohen Konzentrationen einen guten Korrosionsschutz und werden jedoch häufig den oben genannten anwendungstechnischen Erfordernissen nicht gerecht.
- Es wurde nun gefunden, daß man überraschenderweise zu ausgezeichneten Ergebnissen gelangt, wenn man als Korrosionsinhibitoren in wäßrigen Systemen Alkali- und/oder Ammoniumsalze von Verbindungen der Formel I
- Insbesondere sind solche Verbindungen geeignet, bei denen in der oben angeführten Formel I R1 ein Alkylrest mit 3 bis 4 Kohlenstoffatomen und R2 Wasserstoff bedeutet.
- Es wurde weiterhin gefunden, daß neben Alkalisalzen, wie Natrium- oder Kaliumsalze, vorzugsweise Ammoniumsalze mit organischen Basen, wie Ammoniak, Mono-, Di- oder Trialkanolamine, geeignet sind. Insbesondere hat sich dabei Diethanolamin als vorteilhaft ergeben.
- Die erfindungsgemäßen Korrosionsschutzmittel können im übrigen einzeln oder im Gemisch in wäßrigen Lösungen, Dispersionen oder Emulsionen verwendet werden. Bereits bei geringen Konzentrationen ist eine hohe Wirksamkeit vorhanden. Es hat sich nämlich gezeigt, daß teilweise mit 0,5 kg/m3 noch eine ausreichende Wirkung erzielt wird. Somit kommen Mengen von 0,5 bis 10 kg/m3, vorzugsweise 1 bis 10 kg/m3, in Betracht. Die zur Anwendung gelangenden Mittel hesitzen darüber hinaus eine ausgeprägte Schaumarmut und weisen eine gute Wasserhärtestabilität auf.
- Die Herstellung der Aroylcarbonsäuren erfolgt nach an sich bekannten Methoden. Sie können beispielsweise durch Friedel-Crafts-Acylierung von Alkylbenzolen mit entsprechenden cyclischen Anhydriden erhalten werden. Die Herstellung der Aroylcarbonsäuren beziehungsweise deren Salze ist im übrigen nicht Gegenstand der Erfindung.
- Der Anmeldungsgegenstand wird noch durch die nachstehenden Beispiele erläutert, ohne daß er hierauf beschränkt ist.
- Die Bestimmung der Korrosionsschutzeigenschaften erfolgt durch Ermittlung des Massenabtrags. Im einzelnen wird dabei wie folgt gearbeitet :
- Beispiele
- Je drei sorgfältig vorbehandelte und gewogene Teststreifen (unlegierter Stahl, 80 x 15 x 1 mm) wurden in ein 1-1-Gefäß, das 800 ml Testwasser, 50 ml Pufferlösung sowie eine definierte Menge an zu untersuchender Substanz enthält, gehängt und 3 Stunden bei Raumtemperatur und 80 Umdrehungen pro Minute darin belassen.
-
- Das als korrosives Medium benutzte Versuchswasser wurde nach DIN 51360/2 hergestellt und. mit Ammoniak/Ammonium-chlorid gepuffert.
- In der nachstehenden Tabelle 4 sind die Ergebnisse angegeben, die im Vergleich mit Benzolsulfonamidocapronsäure erhalten wurden. Aus den Tabellen 1 bis 3 ist ersichtlich, um welche Verbindungen es sich bei den mit A bis T bezeichneten Produkten gemäß Formel I handelt. Die angegebenen Basen wurden zur Neutralisation der Aroylcarbonsäuren verwendet.
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT84112673T ATE29527T1 (de) | 1983-10-27 | 1984-10-19 | Verwendung von korrosionsinhibitoren in waessrigen systemen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833338953 DE3338953A1 (de) | 1983-10-27 | 1983-10-27 | Verwendung von korrosionsinhibitoren in waessrigen systemen |
DE3338953 | 1983-10-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0144663A1 EP0144663A1 (de) | 1985-06-19 |
EP0144663B1 true EP0144663B1 (de) | 1987-09-09 |
Family
ID=6212843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84112673A Expired EP0144663B1 (de) | 1983-10-27 | 1984-10-19 | Verwendung von Korrosionsinhibitoren in wässrigen Systemen |
Country Status (14)
Country | Link |
---|---|
US (1) | US4909987A (de) |
EP (1) | EP0144663B1 (de) |
JP (1) | JPS60110885A (de) |
AT (1) | ATE29527T1 (de) |
AU (1) | AU568578B2 (de) |
BR (1) | BR8405451A (de) |
CA (1) | CA1261610A (de) |
DE (2) | DE3338953A1 (de) |
DK (1) | DK161896C (de) |
ES (1) | ES8601328A1 (de) |
GR (1) | GR80694B (de) |
NO (1) | NO842824L (de) |
PT (1) | PT79409B (de) |
ZA (1) | ZA848389B (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0212752A1 (de) * | 1985-08-14 | 1987-03-04 | Pumptech N.V. | Verfahren und Zusammensetzung zum Inhibieren der Korrosion von Eisen und Stahl |
EP0412933A1 (de) * | 1989-08-08 | 1991-02-13 | Ciba-Geigy Ag | Überzugszusammensetzungen |
EP0619290A2 (de) * | 1993-04-07 | 1994-10-12 | Ciba-Geigy Ag | Erdalkalimetallsalze, Uebergangsmetallsalze und Uebergangsmetallkomplexe von Ketocarbonsäuren als Korrosionsinhibitoren |
GB2279344A (en) * | 1993-06-25 | 1995-01-04 | Ciba Geigy Ag | Carrier-bound ketocarboxylic acids as corrosion inhibitors |
US5519074A (en) * | 1994-01-18 | 1996-05-21 | Ciba-Geigy Corporation | Complexes of morpholine derivatives with keto-acids as corrosion inhibitors |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3600401A1 (de) * | 1986-01-09 | 1987-07-16 | Henkel Kgaa | Verwendung von alkylbenzoylacrylsaeuren als korrosionsinhibitoren |
US5183842A (en) * | 1989-08-08 | 1993-02-02 | Ciba-Geigy Corporation | Method of producing an organic, corrosion-resistant surface coating |
GB9101468D0 (en) * | 1991-01-23 | 1991-03-06 | Ciba Geigy | Coating compositions |
ZA932674B (en) * | 1992-05-06 | 1995-03-16 | Mintek | The aesthetic enhancement or modification of articles or components made of non-ferrous metals. |
GB2290789B (en) * | 1994-07-01 | 1998-09-16 | Ciba Geigy Ag | Titanium and zirconium complexes of carboxylic acids as corrosion inhibitors |
TW428018B (en) * | 1995-06-29 | 2001-04-01 | Ciba Sc Holding Ag | Aminosilane salts and silanamides of carboxylic acids as corrosion inhibitors |
DK12497A (da) * | 1996-02-12 | 1997-08-13 | Ciba Geigy Ag | Korrisionsinhiberende overtrækssammensætninger til metaller |
MD4245C1 (ro) * | 2012-04-19 | 2014-02-28 | Институт Химии Академии Наук Молдовы | Inhibitor de coroziune a oţelului în apă |
MD4310C1 (ro) * | 2013-07-17 | 2015-06-30 | Институт Химии Академии Наук Молдовы | Inhibitor de coroziune a oţelului în apă |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4366076A (en) * | 1980-06-11 | 1982-12-28 | Ciba-Geigy Corporation | Corrosion inhibited compositions |
JPS6014108B2 (ja) * | 1980-12-31 | 1985-04-11 | 一方社油脂工業株式会社 | 防錆剤 |
IT1210582B (it) * | 1981-10-22 | 1989-09-14 | Roussel Maestretti Spa | Derivati di acido 4-fenil-4-ossobuten-2-oico dotati di proprieta'farmacologiche e composizioni farmaceutiche che li contengono |
JPS59133377A (ja) * | 1983-01-18 | 1984-07-31 | Katayama Chem Works Co Ltd | 水中金属防食方法 |
CA1267746A (en) * | 1983-05-09 | 1990-04-10 | Andreas Lindert | Treatment of metal with derivative of poly- alkenylphenol |
DE3416120A1 (de) * | 1984-04-30 | 1985-10-31 | Henkel KGaA, 4000 Düsseldorf | Benzoylalanine und ihre verwendung als korrosionsinhibitoren fuer waessrige systeme |
-
1983
- 1983-10-27 DE DE19833338953 patent/DE3338953A1/de not_active Withdrawn
-
1984
- 1984-07-11 NO NO842824A patent/NO842824L/no unknown
- 1984-09-28 DK DK466384A patent/DK161896C/da not_active IP Right Cessation
- 1984-10-17 GR GR80694A patent/GR80694B/el unknown
- 1984-10-18 CA CA000465773A patent/CA1261610A/en not_active Expired
- 1984-10-19 EP EP84112673A patent/EP0144663B1/de not_active Expired
- 1984-10-19 AT AT84112673T patent/ATE29527T1/de not_active IP Right Cessation
- 1984-10-19 DE DE8484112673T patent/DE3466018D1/de not_active Expired
- 1984-10-25 PT PT79409A patent/PT79409B/de unknown
- 1984-10-26 ZA ZA848389A patent/ZA848389B/xx unknown
- 1984-10-26 AU AU34723/84A patent/AU568578B2/en not_active Ceased
- 1984-10-26 BR BR8405451A patent/BR8405451A/pt unknown
- 1984-10-26 JP JP59226634A patent/JPS60110885A/ja active Granted
- 1984-10-26 ES ES537133A patent/ES8601328A1/es not_active Expired
-
1988
- 1988-09-06 US US07/241,797 patent/US4909987A/en not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0212752A1 (de) * | 1985-08-14 | 1987-03-04 | Pumptech N.V. | Verfahren und Zusammensetzung zum Inhibieren der Korrosion von Eisen und Stahl |
US5013483A (en) * | 1985-08-14 | 1991-05-07 | Dowell Schlumberger Incorporated | Process and composition for inhibiting iron and steel corrosion |
EP0412933A1 (de) * | 1989-08-08 | 1991-02-13 | Ciba-Geigy Ag | Überzugszusammensetzungen |
EP0619290A2 (de) * | 1993-04-07 | 1994-10-12 | Ciba-Geigy Ag | Erdalkalimetallsalze, Uebergangsmetallsalze und Uebergangsmetallkomplexe von Ketocarbonsäuren als Korrosionsinhibitoren |
US5458678A (en) * | 1993-04-07 | 1995-10-17 | Ciba-Geigy Corporation | Alkaline earth metal salts, transition metal salts and transition metal complexes of ketocarboxylic acids as corrosion inhibitors |
GB2279344A (en) * | 1993-06-25 | 1995-01-04 | Ciba Geigy Ag | Carrier-bound ketocarboxylic acids as corrosion inhibitors |
US5489447A (en) * | 1993-06-25 | 1996-02-06 | Ciba-Geigy Corporation | Carrier-bound ketocarboxylic acids as corrosion inhibitors |
GB2279344B (en) * | 1993-06-25 | 1997-08-13 | Ciba Geigy Ag | Carrier-bound ketocarboxylic acids as corrosion inhibitors |
US5519074A (en) * | 1994-01-18 | 1996-05-21 | Ciba-Geigy Corporation | Complexes of morpholine derivatives with keto-acids as corrosion inhibitors |
Also Published As
Publication number | Publication date |
---|---|
PT79409A (de) | 1984-11-01 |
NO842824L (no) | 1985-04-29 |
DE3466018D1 (en) | 1987-10-15 |
GR80694B (en) | 1985-02-01 |
JPS60110885A (ja) | 1985-06-17 |
DK161896B (da) | 1991-08-26 |
JPH0414193B2 (de) | 1992-03-12 |
ATE29527T1 (de) | 1987-09-15 |
CA1261610A (en) | 1989-09-26 |
BR8405451A (pt) | 1985-09-03 |
ES537133A0 (es) | 1985-10-16 |
DK161896C (da) | 1992-02-03 |
US4909987A (en) | 1990-03-20 |
DE3338953A1 (de) | 1985-05-09 |
AU568578B2 (en) | 1988-01-07 |
AU3472384A (en) | 1985-05-02 |
DK466384A (da) | 1985-04-28 |
PT79409B (de) | 1986-09-08 |
DK466384D0 (da) | 1984-09-28 |
EP0144663A1 (de) | 1985-06-19 |
ZA848389B (en) | 1985-06-26 |
ES8601328A1 (es) | 1985-10-16 |
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