EP0111074B2 - Wäscheweichmachmittelkonzentrat - Google Patents
Wäscheweichmachmittelkonzentrat Download PDFInfo
- Publication number
- EP0111074B2 EP0111074B2 EP83109466A EP83109466A EP0111074B2 EP 0111074 B2 EP0111074 B2 EP 0111074B2 EP 83109466 A EP83109466 A EP 83109466A EP 83109466 A EP83109466 A EP 83109466A EP 0111074 B2 EP0111074 B2 EP 0111074B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- laundry
- carbon atoms
- concentrate
- laundry softener
- spray
- 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
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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
Definitions
- the invention relates to a laundry softener concentrate.
- Laundry softening agents are added to the wash liquor to improve the feel and to increase the softness of textile fabrics.
- Such laundry softeners can be especially cationic tetraalkylammonium compounds and imidazoline derivatives, the effectiveness of which depends on the chemical nature of the alkyl groups.
- laundry softeners are not water-soluble because of these long alkyl residues, they come on the market in the form of a 5-8% aqueous dispersion.
- the large dilution has significant economic disadvantages. Large, bulky and expensive containers are required and, above all, a lot of water is transported. Furthermore, a conceivable automatic dosing in a household washing machine would be made difficult by the large volume of the tanks required.
- US-A-3095373 discloses laundry softener compositions in the form of free-flowing powders which consist of two different laundry softening agents and at least 30% by weight of a finely divided, highly porous silicon-containing composition which has a pH between slightly alkaline and slightly acidic.
- a finely divided, highly porous silicon-containing composition which has a pH between slightly alkaline and slightly acidic.
- Such compositions include: silica gel, diatomaceous earth, fuller's earth, bentonite, finely divided silicic acid, synthetic calcium silicate and mixtures thereof.
- laundry softener concentrates which are also dispersions and have a laundry softener content of 15 to 30%.
- the invention relates to a laundry softener concentrate in the form of a free-flowing powder which consists of a mixture of one or more laundry softeners, synthetically precipitated and spray-dried silica and, if appropriate, one or more solubilizers.
- the laundry softener concentrate can consist solely of the laundry softener and up to 50% by weight of synthetic precipitated and spray-dried silica.
- the laundry softener concentrate can contain 30 to 35% by weight of synthetic precipitated and spray-dried silica. The active substance content is then up to 70%.
- the silica can be both ground and not ground.
- the cationic laundry softening agents present in the laundry softening agent concentrate according to the invention are commercially known products. They are preferably cationic nitrogen-containing compounds, such as quaternary ammonium compounds and amine salts, which have one or two straight-chain organic radicals containing at least 8 carbon atoms, of which at least one radical advantageously contains 12 to 22 carbon atoms.
- Quaternary ammonium compounds of the following formula are preferably present as laundry softeners in the agent according to the invention: wherein R 'for a long chain aliphatic radical with 8 to 22 carbon atoms or a fatty acid ester group, R 2 for a long chain aliphatic radical with 8 to 22 carbon atoms or an alkyl radical with 1 to 6 carbon atoms or an aryl, aryloxy, alkoxy or aralkyl radical 6 to 28 carbon atoms or a fatty acid ester group, R 3 and R 4 represent alkyl or hydroxyalkyl radicals having 1 to 6 carbon atoms or hydroxypolyalkoxyalkyl radicals having 4 to 20 carbon atoms and X is an anion which forms a water-soluble salt, such as a halide (chloride, bromide, iodide) ), Sulfate, methosulfate, acetate, hydroxide anion or a similar inorganic solubilizing mono-
- the nitrogen can be a ring nitrogen and the radicals R 2 and R 3 can be replaced by a ring formed from 4 to 5 carbon atoms. Particularly good results are achieved with those compounds of the formula given in which the radicals R ', R 2 , R 3 and R 4 are each straight-chain aliphatic radicals, such as, for example, alkyl radicals.
- Examples of quaternary ammonium compounds which can be used as laundry softening agents in the laundry softening agent according to the invention are: hydrogenated di-tall oil dimethyl ammonium chloride: ethoxylated distearyl dimethyl ammonium chloride; Dimethyldistearylammonium chloride; Trimethylstearyl ammonium bromide; Cetyltrimethyl ammonium chloride; Dicocodimethyl ammonium chloride; Cetylpyridinium chloride; Alkyldimethylbenzylammonium chloride with higher alkyl group; Diisobutylphenoxyethyldimethylbenzyl ammonium chloride; Laurylisoquinolinium bromide; Distearyldimethylammonium bromide; Distearyldimethylammonium methosulfate; Dimethyl-diacachidylbehenyl-ammonium chloride; Di (soy) dimethyl ammonium chloride; Stearyldimethylbenz
- R 5 is a long-chain aliphatic radical having 8 to 22 carbon atoms
- R 6 is an alkyl radical with 1 to 6 carbon atoms
- R 7 is an alkylamidoalkyl radical with 8 to 22 carbon atoms or a hydroxyalkyl radical with 2 to 6 carbon atoms.
- Examples include 2-heptadecyl-1-methyl-1 - [(2-stearyl-amido) -ethyl] imidazoline methyl sulfate and 2-heptadecyl-1-hydroxyethylimidazoline chloride.
- Examples of amines which can be used in the form of their water-soluble salts in the laundry softening agent according to the invention are primary tall oil amine, primary cocoamine, primary hydrogenated tall oil amine, tall oil 1,3-propylene diamine, ole 1,3-propylene diamine and coco 1,3-propylene diamine .
- the particularly useful water-soluble salts of the amines listed above are, for example, the sulfate, the hydrogen sulfate and the chloride.
- the term "Coco" stands for fatty acid groups that are present in the fatty acids of coconut oil. Such acids contain 8 to 18 carbon atoms per molecule; the acids with 12 to 14 carbon atoms predominate.
- the laundry softener concentrates according to the invention can contain up to a total of 35% by weight of a solubilizer and water, based on the amount of laundry softener.
- solubilizers can be used as solubilizers: isopropanol, ethanol, glycol, benzenesulfonates, toluenesulfonates, xylenesulfonates or wetting agents, e.g. nonionic surfactants such as nonylphenol ethoxylates, fatty alcohol ethoxylates and others
- the laundry softener concentrate according to the invention is a free-flowing powder. It can be stored and, due to its powdery nature, requires only a small packaging space. It is easy to dose and can be combined with detergent if necessary.
- the laundry softener concentrate obtained is a free-flowing powder.
- the laundry softener concentrate obtained is a free-flowing powder.
- the silica Sipernat 22 used is a precipitated and spray-dried silica. It has the following physico-chemical characteristics:
- the Sipernat 22 S silica used is a spray-dried and ground precipitated silica with the following physico-chemical characteristics:
- the Sipernat 50 and 50 S silicas used are spray-dried precipitated silica with the following physico-chemical data:
Description
- Die Erfindung betrifft ein Wäscheweichmachmittelkonzentrat.
- Wäscheweichmachmittel werden zur Griffverbesserung und zur Erhöhung der Weichheit von textilen Geweben der Waschflotte zugesetzt. Derartige Wäscheweichmachmittel können vorallem kationische Tetraalkylammoniumverbindungen und Imidazolinderivate sein, deren Wirksamkeit von der chemischen Beschaffenheit der Alkylgruppen abhängt.
- Da die Wäscheweichmachmittel wegen dieser langen Alkylreste nicht wasserlöslich sind, kommen sie in Form einer 5-8 %igen wässrigen Dispersion in den Handel. Die grosse Verdünnung hat deutliche wirtschaftliche Nachteile. Es sind grosse, unhandliche und teure Gebinde erforderlich und vor allem wird sehr viel Wasser transportiert. Ferner würde eine denkbare automatische Dosierung in einer Haushaltswaschmaschine durch das große Volumen der erforderlichen Tanks erschwert.
- Aus der US-A- 3095373 sind Wäscheweichmacherkompositionen in Form frei fliessender Pulver bekannt, die aus zwei verschiedenen Wäschweichmachmitteln und zu mindestens 30 Gew.% aus einer fein verteilten, hochporösen siliciumhaltigen Zusammensetzung, die einen pH zwischen schwach alkalisch und leicht sauer hat, besteht. Als Beispiele für solche Zusammensetzungen sind genannt: Silicagel, Diatomeenerde, Fullererde, Bentonit, fein verteilte Keiselsäure, synthetisches Calciumsilicat und Gemische derselben.
- Es ist bekannt, Wäscheweichmachmittelkonzentrate die ebenfalls Dispersionen sind und einen Gehalt an Wäscheweichmachmittel von 15 bis 30-% aufweisen, zu verwenden.
- Diese bekannten Wäscheweichmachmittelkonzentrate weisen jedoch mit zunehmender Konzentration eine exponentiell steigende Viskosität auf (Tenside Detergents 18 (1981) 5 S.243-246).
- Gegenstand der Erfindung ist ein Wäscheweichmachmittelkonzentrat in Form eines rieselfähigen Pulvers, welches aus einer Mischung von einem oder mehreren Wäscheweichmachmitteln, synthetischer gefällter und sprühgetrockneter Kieselsäure und gegebenenfalls einem oder mehrerem Lösungsvermittlern besteht.
- In einer besonderen Ausführungsform der Erfindung kann das Wäscheweichmachmittelkonzentrat allein aus dem Wäscheweichmachmittel und bis zu 50 Gew.-% synthetischer gefällter und sprühgetrockneter Kieselsäure bestehen.
- In einer bevorzugten Ausführungsform kann das Wäscheweichmachmittelkonzentrat 30 bis 35 Gew.-% synthetischer gefällter und sprühgetrockneter Kieselsäure enthalten. Der Aktivsubstanzgehalt beträgt dann bis zu 70%.
- Die Kieselsäure kann sowohl vermahlen als auch nicht vermahlen sein.
- Die in dem erfindungsgemäßen Wäscheweichmachmittelkonzentrat vorhandenen kationischen Wäscheweichmachmittel sind haldelsübliche bekannte Produkte. Es handelt sich vorzugsweise um kationische stickstoffhaltige Verbindungen, wie quaternäre Ammoniumverbindungen und Aminsalze, die ein oder zwei wenigstens 8 Kohlenstoffatome aufweisende gradkettige organische Reste besitzen, von denen vorteilhaft wenigstens ein Rest 12 bis 22 Kohlenstoffatome enthält. Bevorzugt sind in dem erfindungsgemäßen Mittel als Wäscheweichmacher quartäre Ammoniumverbindungen der folgenden Formel vorhanden:
- Als Wäscheweichmacher sind auch Verbindungen der Formel:
- Beispiele für Amine, die in Form ihrer wasserlöslichen Salze im erfindungsgemäßen Wäscheweichmachmittel verwendet werden können sind primäres Tallölamin, primäres Cocoamin, primäres hydriertes Tallölamin, Tallöl-1,3-propylendiamin, Olyl-1,3-propylendiamin und Coco-1,3-propylendiamin. Die besonders gut brauchbaren wasserlöslichen Salze der zuvor aufgeführten Amine sind beispielsweise das Sulfat, das Hydrogensulfat und das Chlorid. Die Benennung "Coco" steht für Fettsäuregruppen, die in den Fettsäuren des Kokosnußöls vorhanden sind. Solche Säuren enthalten 8 bis 18 Kohlenstoffatome je Molekül; es überwiegen dabei die Säuren mit 12 bis 14 Kohlenstoffatomen.
- Die erfindungsgemäßen Wäscheweichmachmittelkonzentrate können bis zu insgesamt 35 Gew.-% eines Lösungsvermittlers und Wasser, bezogen auf die Menge an Wäscheweichmachmittel, enthalten.
- Als Lösungsvermittler können eingesetzt werden: Isopropanol, Ethanol, Glykol, Benzolsulfonate, Toluolsulfonate, Xylolsulfonate oder Netzmittel, wie z.B. nichtionische Tenside, wie Nonylphenolethoxylate, Fettalkoholethoxylate u.a.
- Das erfindungsgemäße Wäscheweichmachmittelkonzentrat ist ein leicht rieselfähiges Pulver. Es ist lagerfähig und beansprucht auf Grund seiner pulverförmigen Beschaffenheit nut einen geringen Verpackungsraum. Es läßt sich leicht dosieren und kann gegebenenfalls mit Waschmittel kombiniert werden.
-
- 1. Das Wäscheweichmachmittel REWOQUATO CR 3099 (100%) (=Difettsäureesterdimethylammoniummethosulfat) wird auf 60°C erhitzt und mit 31 Gew,.% Sipernat 22 S vermischt. Das erhaltene Wäscheweichmachmittelkonzentrat ist ein rieselfähiges Pulver.
- 2. Die 75 %ige Wäscheweichmachmitteldispersion REWOQUATO W 7500 (75%) (=quarternäre Imidazoliniumdialkylverbindung 75% mit 25% lsopropanol) wird mit 34 Gew.-% Sipernat 22 vermischt. Das erhaltene Wäscheweichmachmittelkonzentrat ist ein rieselfähiges Pulver.
- 3. Die 75 %ige Wäscheweichmachmitteldispersion REWOQUAT@ W 7500 H wird zuerst aufgeschmolzen und dann mit 35% Sipernat 50 vermischt.
- Das erhaltene Wäscheweichmachmittelkonzentrat ist ein rieselfähiges Pulver.
- 4. Die 75 % Wäscheweichmachmitteldispersion Präpagen WK(=Distearyldimethylammoniumchlorid) wird mit 32% Sipernat 50 S vermischt.
- Das erhaltene Wäscheweichmachmittelkonzentrat ist ein rieselfähiges Pulver.
-
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Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT83109466T ATE25402T1 (de) | 1982-11-27 | 1983-09-23 | Waescheweichmachmittelkonzentrat. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3243983A DE3243983C2 (de) | 1982-11-27 | 1982-11-27 | Wäscheweichmachmittelkonzentrat |
DE3243983 | 1982-11-27 |
Publications (4)
Publication Number | Publication Date |
---|---|
EP0111074A2 EP0111074A2 (de) | 1984-06-20 |
EP0111074A3 EP0111074A3 (en) | 1985-08-14 |
EP0111074B1 EP0111074B1 (de) | 1987-02-04 |
EP0111074B2 true EP0111074B2 (de) | 1990-04-18 |
Family
ID=6179241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83109466A Expired - Lifetime EP0111074B2 (de) | 1982-11-27 | 1983-09-23 | Wäscheweichmachmittelkonzentrat |
Country Status (7)
Country | Link |
---|---|
US (1) | US4589989A (de) |
EP (1) | EP0111074B2 (de) |
JP (1) | JPS59106575A (de) |
AT (1) | ATE25402T1 (de) |
CA (1) | CA1226704A (de) |
DE (2) | DE3243983C2 (de) |
IL (1) | IL70057A (de) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3243983C2 (de) * | 1982-11-27 | 1984-11-22 | Degussa Ag, 6000 Frankfurt | Wäscheweichmachmittelkonzentrat |
DE3402437A1 (de) * | 1984-01-25 | 1985-07-25 | Rewo Chemische Werke Gmbh, 6497 Steinau | Pulverfoermiges waescheweichspuelmittel, verfahren zu seiner herstellung und diese enthaltendes waschmittel |
DE3416472A1 (de) * | 1984-05-04 | 1985-11-07 | Hoechst Ag, 6230 Frankfurt | Weichmacher enthaltende waschmittel |
DE3434709A1 (de) * | 1984-09-21 | 1986-04-03 | Hoechst Ag, 6230 Frankfurt | Adsorbentien auf basis organophil modifizierter schichtkieselsaeuren |
JPH0742649B2 (ja) * | 1987-05-26 | 1995-05-10 | 花王株式会社 | 柔軟仕上剤 |
NZ235490A (en) * | 1989-10-16 | 1993-08-26 | Colgate Palmolive Co | Fabric-softening compositions |
US5185088A (en) * | 1991-04-22 | 1993-02-09 | The Procter & Gamble Company | Granular fabric softener compositions which form aqueous emulsion concentrates |
GB9209170D0 (en) * | 1992-04-28 | 1992-06-10 | Unilever Plc | Rinse conditioner |
WO1994007979A1 (en) * | 1992-09-28 | 1994-04-14 | The Procter & Gamble Company | Method for using solid particulate fabric softener in automatic dosing dispenser |
US5458799A (en) * | 1993-08-03 | 1995-10-17 | Amway Corporation | Mix process for formulating detergents |
GB9406824D0 (en) * | 1994-04-07 | 1994-06-01 | Unilever Plc | Fabric softening composition |
CA2184070C (en) * | 1994-04-07 | 2001-05-01 | Ziya Haq | Fabric softening composition |
US5714450A (en) * | 1996-03-15 | 1998-02-03 | Amway Corporation | Detergent composition containing discrete whitening agent particles |
WO1997033957A1 (en) * | 1996-03-15 | 1997-09-18 | Amway Corporation | Powder detergent composition having improved solubility |
US5714451A (en) * | 1996-03-15 | 1998-02-03 | Amway Corporation | Powder detergent composition and method of making |
WO1997033958A1 (en) * | 1996-03-15 | 1997-09-18 | Amway Corporation | Discrete whitening agent particles, method of making, and powder detergent containing same |
US6177397B1 (en) | 1997-03-10 | 2001-01-23 | Amway Corporation | Free-flowing agglomerated nonionic surfactant detergent composition and process for making same |
DE19721885A1 (de) * | 1997-05-26 | 1998-12-03 | Henkel Kgaa | Verfahren zur Herstellung kationtensidhaltiger Granulate |
US6130193A (en) * | 1998-02-06 | 2000-10-10 | Precision Fabrics Group, Inc. | Laundry detergent compositions containing silica for laundry detergent sheets |
US5990423A (en) * | 1998-05-28 | 1999-11-23 | Eze Weigh, Llc | Mobile hospital bed scale |
US7232962B2 (en) * | 1998-05-28 | 2007-06-19 | Richard Rynd | Mobile hospital bed scale |
GB0207484D0 (en) | 2002-03-28 | 2002-05-08 | Unilever Plc | Solid fabric conditioning compositions |
GB0207481D0 (en) | 2002-03-28 | 2002-05-08 | Unilever Plc | Solid fabric conditioning compositions |
GB0207483D0 (en) | 2002-03-28 | 2002-05-08 | Unilever Plc | Fabric conditioning compositions |
EP1502942A1 (de) * | 2003-07-29 | 2005-02-02 | Clariant International Ltd. | Feste Weichspülerzusammensetzung |
CA2562107C (en) | 2004-04-09 | 2012-10-16 | Unilever Plc | Granulate for use in a cleaning product and process for its manufacture |
US20070130694A1 (en) * | 2005-12-12 | 2007-06-14 | Michaels Emily W | Textile surface modification composition |
US7655609B2 (en) | 2005-12-12 | 2010-02-02 | Milliken & Company | Soil release agent |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3095373A (en) * | 1959-01-30 | 1963-06-25 | Wyandotte Chemicals Corp | Fabric softeners |
US3546115A (en) * | 1967-02-28 | 1970-12-08 | Cargill Inc | Fabric softener |
US3573091A (en) * | 1967-11-13 | 1971-03-30 | Armour & Co | Method of preparing water-dispersible softener compositions and products thereby |
US3533942A (en) * | 1968-04-29 | 1970-10-13 | American Potash & Chem Corp | Process for loading expanded water-solution hydrate salt particles |
JPS4835637B1 (de) * | 1970-12-23 | 1973-10-29 | ||
US4001123A (en) * | 1972-09-11 | 1977-01-04 | Colgate-Palmolive Company | Fabric softener compositions containing N-alkyl-1,3-propylene diamine treated with maleic anhydride |
US3977980A (en) * | 1974-01-04 | 1976-08-31 | American Can Company | Solid fabric conditioner composition |
LU71307A1 (de) * | 1974-11-18 | 1976-09-06 | ||
US4255294A (en) * | 1975-04-01 | 1981-03-10 | Lever Brothers | Fabric softening composition |
LU75088A1 (de) * | 1976-06-04 | 1978-01-18 | ||
US4025444A (en) * | 1975-08-18 | 1977-05-24 | The Procter & Gamble Company | Fabric softening agents |
US4155855A (en) * | 1977-07-06 | 1979-05-22 | The Procter & Gamble Company | Concentrated liquid fabric softener composition |
US4199465A (en) * | 1977-12-23 | 1980-04-22 | The Procter & Gamble Company | Laundry detergent substrate articles |
EP0026528B2 (de) * | 1979-09-29 | 1992-08-19 | THE PROCTER & GAMBLE COMPANY | Reinigungsmittelzusammensetzungen |
DE3066202D1 (en) * | 1979-11-03 | 1984-02-23 | Procter & Gamble | Granular laundry compositions |
JPS604879B2 (ja) * | 1981-02-20 | 1985-02-07 | 花王株式会社 | 洗浄剤組成物 |
US4392965A (en) * | 1981-11-12 | 1983-07-12 | Woodward Fred E | Laundry softener antistatic composition |
US4417999A (en) * | 1982-06-03 | 1983-11-29 | Witco Chemical Corporation | Free flowing antistatic composition |
GB2124644B (en) * | 1982-07-05 | 1986-03-19 | Lion Corp | Method for granulating cationic surfactant |
DE3243983C2 (de) * | 1982-11-27 | 1984-11-22 | Degussa Ag, 6000 Frankfurt | Wäscheweichmachmittelkonzentrat |
DE3402437A1 (de) * | 1984-01-25 | 1985-07-25 | Rewo Chemische Werke Gmbh, 6497 Steinau | Pulverfoermiges waescheweichspuelmittel, verfahren zu seiner herstellung und diese enthaltendes waschmittel |
-
1982
- 1982-11-27 DE DE3243983A patent/DE3243983C2/de not_active Expired
-
1983
- 1983-09-23 DE DE8383109466T patent/DE3369699D1/de not_active Expired
- 1983-09-23 AT AT83109466T patent/ATE25402T1/de not_active IP Right Cessation
- 1983-09-23 EP EP83109466A patent/EP0111074B2/de not_active Expired - Lifetime
- 1983-10-26 IL IL70057A patent/IL70057A/xx unknown
- 1983-11-25 CA CA000441938A patent/CA1226704A/en not_active Expired
- 1983-11-25 JP JP58220823A patent/JPS59106575A/ja active Granted
-
1984
- 1984-11-16 US US06/672,164 patent/US4589989A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH0152506B2 (de) | 1989-11-09 |
EP0111074A2 (de) | 1984-06-20 |
DE3369699D1 (en) | 1987-03-12 |
IL70057A (en) | 1987-10-30 |
JPS59106575A (ja) | 1984-06-20 |
IL70057A0 (en) | 1984-01-31 |
DE3243983C2 (de) | 1984-11-22 |
EP0111074B1 (de) | 1987-02-04 |
ATE25402T1 (de) | 1987-02-15 |
CA1226704A (en) | 1987-09-15 |
EP0111074A3 (en) | 1985-08-14 |
US4589989A (en) | 1986-05-20 |
DE3243983A1 (de) | 1984-05-30 |
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