EP0040713A1 - Use of mixed formals of alkylpolyglycol ethers as foam suppressing agents - Google Patents
Use of mixed formals of alkylpolyglycol ethers as foam suppressing agents Download PDFInfo
- Publication number
- EP0040713A1 EP0040713A1 EP81103326A EP81103326A EP0040713A1 EP 0040713 A1 EP0040713 A1 EP 0040713A1 EP 81103326 A EP81103326 A EP 81103326A EP 81103326 A EP81103326 A EP 81103326A EP 0040713 A1 EP0040713 A1 EP 0040713A1
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- European Patent Office
- Prior art keywords
- carbon atoms
- mixed formals
- agents
- formula
- alkyl
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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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
-
- 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
- C11D3/0026—Low foaming or foam regulating compositions
Definitions
- the invention relates to the use of certain alkyl polyglycol ether mixed formals as anti-foaming agents in strongly alkaline cleaning agents.
- Industrial cleaning agents in particular those which are used in automatic systems for cleaning rigid surfaces such as metal, ceramic or glass and in particular for bottle cleaning, are said to have low foaming power with a strong cleaning power exhibit.
- the industrial cleaning agents of the type mentioned are mostly products which contain strongly alkaline substances such as, in particular, alkali metal hydroxides or also alkali metal silicates or alkali metal orthophosphates, individually or in a mixture. In the case of such products, high demands are placed on the defoamers not only with regard to the anti-foam effect but also with regard to the storage stability in the corresponding solid products.
- alkyl polyglycol ether mixed formals of the formula are used as anti-foaming agents in alkaline cleaning agents in which R 1 is a straight-chain or branched alkyl or alkylene radical having 8 to 22 carbon atoms, R 2 is a straight-chain or branched alkyl radical having 1 to 5 carbon atoms, m is a number from 2 to 30 and n is a number from 1 to 3.
- R 1 is an alkyl radical having 12 to 18 carbon atoms
- R 2 is an alkyl radical having 2 to 4 carbon atoms
- m is an integer from 7 to 15
- n is 1.
- the alkyl polyglycol ether mixed formals of the formula given above which are used can be prepared, for example by reaction of fatty alcohol ethoxylate of the formula with a di-alkyl glycol formal of the formula in the presence of a strong acid, such as sulfuric acid, by heating to temperatures of about 150 ° C. for several hours.
- R 1 and R 2 have the same meaning as given in formula I.
- Suitable starting products for the fatty alcohol ethoxylates are straight-chain or branched aliphatic alcohols, such as hexadecyl, tetradecyl and octadecyl alcohols, and the corresponding branched iso alcohols.
- Branched aliphatic alcohols which can be prepared by the so-called Guerbet reaction (dimerization of primary alcohols) can also be used.
- synthetic fatty alcohols or mixtures thereof, such as those obtained in oxo synthesis can also be used.
- the strongly alkaline cleaning agents (pH above 10) contain sodium or potassium hydroxide in particular.
- other strongly alkaline substances such as alkali carbonate and alkali orthophosphates, are used alone or in a mixture with alkali hydroxides.
- the alkaline cleaning agents can also contain the usual constituents, such as alkali silicates, alkali borates, polymeric alkali phosphates and / or complexing agents, such as phosphonic acids, in particular 1-hydroxy ethane-1,1-diphosphonic acid, aminotrimethylene phosphonic acid or 2-phosphonobutane-1,2,4-tricarboxylic acid.
- the molar ratio of Na 2 O or K 2 0: P 2 O 5 can be 1: 1 to 2: 1.
- sodium tripolyphosphate is used.
- Fine-particle synthetically produced, water - insoluble, bound water-containing aluminosilicates of the general formula can also be used as substitutes for the polyphosphates in the cat a cation of valence n, preferably sodium, exchangeable for calcium, x a number from 0.7 to 1.5, preferably 0.9 to 1.3, and y a number from 0.8 to 6, preferably of 1 , 3 to 4, which have a calcium binding capacity of 50 to 200, preferably 100 to 200 mg CaO / g of the anhydrous aluminosilicate can be used.
- aluminosilicates can be crystalline or X-ray amorphous.
- the crystalline sodium aluminosilicates are preferred, in particular the zeolites A and X.
- alkali stable anionic surfactants such as alkyl and / or aryl sulfonates, are also suitable as constituents.
- the amount of anti-foaming agent added is about 0.1 to 1 g / l, based on the solution used. The amount added depends on the desired antifoam effect and the impurities or bath concentration of the cleaning agent.
- the detergents are generally used with a bath concentration of 0.2 to 10% depending on the intended use.
- the application temperature is generally between 40 and 90 ° C.
- the cleaning agents prepared in this way were each stored in closed polypropylene containers at 45 ° C. and the defoamer tests were carried out at intervals of 2 weeks each.
- the free fall cycle method consists of heating 500 ml of cleaning solution to 60 ° C in a jacketed 2-1 measuring cylinder.
- this solution is put into constant circulation at a throughput capacity of 4 l / minute so that the solution is sucked from the bottom of the measuring cylinder with a glass tube and in the open via a second glass tube with the 2000 ml mark of the measuring cylinder Case traced. becomes.
- a constant initial foam volume for example 2000 ml
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Degasification And Air Bubble Elimination (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Alkylpolyglykolethermischformale der Formel R1 - O - (CH2CH2O)m - CH2 - (OCH2CH2)n - O - R2 in der R1 einen geradkettigen oder verzweigten Alkyl- oder Alkylenrest mit 8 bis 22 Kohlenstoffatomen, R2 einen geradkettigen oder verzweigten Alkylrest mit 1 bis 5 Kohlenstoffatomen, m eine Zahl von 2 bis 30 und n eine Zahl von 1 bis 3 bedeuten, werden als Antischaummittel in alkalischen Reinigungsmitteln verwendet. Die alkalistabilen Mischformale werden den alkalischen Reinigungsmitteln in einer Menge von 0,1 bis 1 g/l, bezogen auf die zur Anwendung kommende Lösung, zugesetzt. Die gut dispergierbaren Antischaummittel sind biologisch abbaubar.Alkyl polyglycol ether mixed formals of the formula R1 - O - (CH2CH2O) m - CH2 - (OCH2CH2) n - O - R2 in which R1 is a straight-chain or branched alkyl or alkylene radical having 8 to 22 carbon atoms, R2 is a straight-chain or branched alkyl radical having 1 to 5 carbon atoms , m is a number from 2 to 30 and n is a number from 1 to 3, are used as anti-foaming agents in alkaline cleaning agents. The alkali-stable mixed formals are added to the alkaline cleaning agents in an amount of 0.1 to 1 g / l, based on the solution used. The highly dispersible anti-foaming agents are biodegradable.
Description
Gegenstand der Erfindung ist die Verwendung bestimmter Alkylpolyglykolethermischformale als Antischaummittel in stark alkalischen Reinigungsmitteln.iIndustrielle Reinigungsmittel, insbesondere solche, die in automatischen Anlagen zur Reinigung von starren Oberflächen wie Metall, Keramik oder Glas sowie insbesondere zur Flaschenreinigung eingesetzt werden, sollen bei starker Reinigungskraft eine geringe Schaumentwicklung aufweisen. Bei den industriellen Reinigungsmitteln der genannten Art handelt es sich meist um Produkte, die stark alkalische Stoffe wie insbesondere Alkalihydroxide oder auch Alkalisilikate oder Alkaliorthophosphate einzeln oder im Gemisch enthalten. Bei derartigen Produkten werden an die Entschäumer nicht nur hinsichtlich der Antischaumwirkung sondern auch hinsichtlich der Lagerstabilität in den entsprechenden festen Produkten hohe Anforderungen gestellt.The invention relates to the use of certain alkyl polyglycol ether mixed formals as anti-foaming agents in strongly alkaline cleaning agents. Industrial cleaning agents, in particular those which are used in automatic systems for cleaning rigid surfaces such as metal, ceramic or glass and in particular for bottle cleaning, are said to have low foaming power with a strong cleaning power exhibit. The industrial cleaning agents of the type mentioned are mostly products which contain strongly alkaline substances such as, in particular, alkali metal hydroxides or also alkali metal silicates or alkali metal orthophosphates, individually or in a mixture. In the case of such products, high demands are placed on the defoamers not only with regard to the anti-foam effect but also with regard to the storage stability in the corresponding solid products.
Es ist bekannt, sowohl in festen als auch in flüssigen Produkten für die industrielle Reinigung, Anlagerungsprodukte von Ethylenoxid und Propylenoxid an Verbindungen wie Fettalkohole, Fettsäuren, Polyglycerin und Ethylendiamine als Entschäumer einzusetzen. Es hat sich jedoch gezeigt, daß bei der Konfektionierung beispielsweise in festen Reinigungsmitteln, die einen sehr hohen Alkaligehalt, insbesondere an über 50 % und mehr Ätzalkali enthalten die Lagerstabilität nicht immer hinreichend ist. Auch ist es erwünscht, daß die Antischaummittel eine gute biologische Abbaubarkeit besitzen, laugenstabil sind, indem sie während des Reinigungsprozesses unter andauernder Temperaturbelastung ihre Wirksamkeit nicht verlieren.It is known to use both in solid and in liquid products for industrial cleaning, adducts of ethylene oxide and propylene oxide with compounds such as fatty alcohols, fatty acids, polyglycerol and ethylenediamines as defoamers. However, it has been shown that the storage stability is not always sufficient in the case of packaging, for example in solid cleaning agents which contain a very high alkali content, in particular more than 50% and more caustic alkali. It is also desirable that the anti-foaming agents have good biodegradability, are alkali-stable, so that they do not lose their effectiveness during the cleaning process under constant exposure to temperature.
Es wurde nun gefunden, daß in besonderem Maße die Anforderungen an die Alkalistabilität und die Dispergierbarkeit und biologische Abbaubarkeit erfüllt werden, wenn man als Antischaummittel in alkalischen Reinigungsmitteln Alkylpolyglykolethermischformale der Formel
Insbesondere hat sich die Verwendung der Verbindungen der Formel I als geeignet erwiesen, in der R1 einen Alkylrest mit 12 bis 18 Kohlenstoffatomen, R2 einen Alkylrest mit 2 bis 4 Kohlenstoffatomen, m eine ganze Zahl von 7 bis 15 und n gleich 1 ist. Die zur Anwendung gelangenden Alkylpolyglykolethermischformale der oben angegebenen Formel können hergestellt werden, beispielsweise durch Umsetzung von Fettalkoholethoxilat der Formel
Als Ausgangsprodukte für die Fettalkoholethoxilate kommen gradkettige oder auch verzweigte aliphatische Alkohole, wie Hexadecyl-, Tetradecyl- und Octadecylalkohole sowie die entsprechenden verzweigten Isoalkohole in Betracht. Auch können als verzweigte aliphatische Alkohole solche verwendet werden, die durch die sogenannte Guerbet-Reaktion (Dimerisierung von primären Alkoholen) herstellbar sind. Es können jedoch auch synthetische Fettalkohole oder Gemische davon, wie sie bei der Oxosynthese anfallen, Anwendung finden.Suitable starting products for the fatty alcohol ethoxylates are straight-chain or branched aliphatic alcohols, such as hexadecyl, tetradecyl and octadecyl alcohols, and the corresponding branched iso alcohols. Branched aliphatic alcohols which can be prepared by the so-called Guerbet reaction (dimerization of primary alcohols) can also be used. However, synthetic fatty alcohols or mixtures thereof, such as those obtained in oxo synthesis, can also be used.
Die stark alkalischen Reinigungsmittel (pH-Wert über 10) enthalten insbesondere Natrium- oder Kaliumhydroxid. Es werden jedoch auch andere stark alkalisch reagierende Stoffe, wie Alkalicarbonat und Alkaliorthophosphate, allein oder im Gemisch mit Alkalihydroxiden, verwendet. Die alkalischen Reinigungsmittel können jedoch darüber hinaus auch die üblichen Bestandteile, wei Alkalisilikate, Alkaliborate, polymere Alkaliphosphate und/oder Komplexbildner, wie Phosphonsäuren, insbesondere 1-Hydroxyethan-1,1-diphosphonsäure, Aminotrimethylenphosphonsäure oder 2-Phosphono-butan-1,2,4-tricarbonsäure, enthalten.The strongly alkaline cleaning agents (pH above 10) contain sodium or potassium hydroxide in particular. However, other strongly alkaline substances, such as alkali carbonate and alkali orthophosphates, are used alone or in a mixture with alkali hydroxides. However, the alkaline cleaning agents can also contain the usual constituents, such as alkali silicates, alkali borates, polymeric alkali phosphates and / or complexing agents, such as phosphonic acids, in particular 1-hydroxy ethane-1,1-diphosphonic acid, aminotrimethylene phosphonic acid or 2-phosphonobutane-1,2,4-tricarboxylic acid.
Bei den polymeren Phosphaten kann das Molverhältnis von Na2O oder K 2 0 : P2O5 1: 1 bis 2 : 1 betragen. Insbesondere wird Natriumtripolyphosphat verwendet.In the polymeric phosphates, the molar ratio of Na 2 O or K 2 0: P 2 O 5 can be 1: 1 to 2: 1. In particular, sodium tripolyphosphate is used.
Als Substitute für die Polyphosphate können auch feinteilige synthetisch hergestellte, wasserunlös- liche, gebundenes Wasser enthaltende Alumosilikate der allgemeinen Formel
Ferner kommen in besonderen Fällen Alkali stabile anionische Tenside, wie Alkyl- und/oder Arylsulfonate, als Bestandteile in Betracht.In special cases, alkali stable anionic surfactants, such as alkyl and / or aryl sulfonates, are also suitable as constituents.
Die zugesetzte Menge an Antischaummittel beträgt etwa 0,1 bis 1 g/l, bezogen auf die zur Anwendung gelangende Lösung. Die Zusatzmenge richtet sich nach der gewünschten Antischaumwirkung und nach den Verunreinigungen beziehungsweise der Badkonzentration des Reinigungsmittels. Die Reinigungsmittel werden im allgemeinen mit einer Badkonzentration von 0,2 bis 10 % je nach dem Verwendungszweck eingesetzt. Die Anwendungstemperatur liegt im allgemeinen zwischen 40 und 90°C.The amount of anti-foaming agent added is about 0.1 to 1 g / l, based on the solution used. The amount added depends on the desired antifoam effect and the impurities or bath concentration of the cleaning agent. The detergents are generally used with a bath concentration of 0.2 to 10% depending on the intended use. The application temperature is generally between 40 and 90 ° C.
Durch intensives Vermischen der Bestandteile wurden verschiedene Reinigungsmittel, wie sie insbesondere für die Flaschenreinigung üblich sind, hergestellt. Diese hatten die folgende Zusammensetzung:
- a) 75 % technisches Natriumhydroxid in Schuppenform 6 % Natriumtripolyphosphat 15,5 % Natriummetasilikat . 5 Hydrat sowie jeweils 3,5 % des zu prüfenden Entschäumers
- b) 15 % Natriumhydroxid 25 % Natriumtripolyphosphat 25 % Natriummetasilikat. 32 % Natriumcarbonat 3 % des zu prüfenden Entschäumers
- a) 75% technical sodium hydroxide in the form of flakes 6% sodium tripolyphosphate 15.5% sodium metasilicate. 5 hydrate and 3.5% each of the defoamer to be tested
- b) 15% sodium hydroxide 25% sodium tripolyphosphate 25% sodium metasilicate. 32% sodium carbonate 3% of the defoamer to be tested
Die so hergestellten Reinigungsmittel wurden jeweils bei 45°C in verschlossenen Behältern aus Polypropylen gelagert und die Entschäumerteste in Zeitabständen von je 2 Wochen durchgeführt.The cleaning agents prepared in this way were each stored in closed polypropylene containers at 45 ° C. and the defoamer tests were carried out at intervals of 2 weeks each.
Zur Prüfung wurden je 1,5 % der Reinigermischung in jeweils eine 0,025%ige Schmierseifen- beziehungsweise 0,025%ige Alkylbenzolsulfonat-Lösung eingeführt. Je 500 ml dieser Lösungen wurden anschließend nach der Freifallkreislaufmethode geprüft und die Schaumwerte bestimmt.For testing, 1.5% of the detergent mixture was introduced into a 0.025% lubricating soap and 0.025% alkylbenzenesulfonate solution. Each 500 ml of these solutions were then tested using the free-fall cycle method and the foam values were determined.
Die Freifallkreislaufmethode besteht darin, daß 500 ml Reinigerlösung in einem ummantelten 2-1-Meßzylinder auf 60°C erhitzt werden.The free fall cycle method consists of heating 500 ml of cleaning solution to 60 ° C in a jacketed 2-1 measuring cylinder.
Mit Hilfe einer Pumpe wird diese Lösung bei einer Durchlaufkapazität von 4 1/Minute so in einen ständigen Umlauf gebracht, daß die Lösung mit einem Glasrohr vom Boden des Meßzylinders angesaugt und über ein zweitesj mit der 2000-ml-Marke des Meßzylinders abschließendes Glasrohr im freien Fall zurückgeführt. wird. Nach kurzer Laufzeit stellt sich hierbei ein konstantes Ausgangsschaumvolumen (zum Beispiel 2000 ml) ein.With the help of a pump, this solution is put into constant circulation at a throughput capacity of 4 l / minute so that the solution is sucked from the bottom of the measuring cylinder with a glass tube and in the open via a second glass tube with the 2000 ml mark of the measuring cylinder Case traced. becomes. After a short running time, a constant initial foam volume (for example 2000 ml) is established.
Die sich ergebenden Gesamtvolumina, Schaum und Lösung, wurden in Abständen von 1, 3, 5, 10, 20 und 30 Minuten äbgelesen.The resulting total volumes, foam and solution, were read at 1, 3, 5, 10, 20 and 30 minute intervals.
Bei den Produkten, die nicht oder nur beschränkt nach einer mehrwöchigen Lagerzeit stabil sind, tritt entweder keine schaumdrückende Wirkung auf oder die Schaumdepression nimmt nach kurzer Zeit, zum Beispiel innerhalb 10 bis 30 Minuten, erheblich ab. Bei stabilen Produkten bleibt die Antischaumwirkung von Anfang an bis zum Ende der Prüfzeit (30 Minuten) praktisch konstant. Bei instabilen Produkten erreicht. der Schaum nach wenigen Minuten seine maximale Höhe, zum Beispiel 2000 ml.For products that are not stable or only stable to a limited extent after a storage period of several weeks, either there is no foam-suppressing effect or the foam depression decreases considerably after a short time, for example within 10 to 30 minutes. In the case of stable products, the anti-foam effect remains practically constant from the beginning to the end of the test period (30 minutes). Achieved for unstable products. the foam reaches its maximum height after a few minutes, for example 2000 ml.
Die nachstehende Tabelle gibt einen Überblick über die Stabilität und Entschäumerwirkung der erfindungsgemäßen Produkte im Vergleich mit ähnlichen Handelsprodukten.
Ein Mittel zur Dampfstrahlreinigung von metallischen Oberflächen hatte folgende Zusammensetzung:
- 51 % Wasser
- 5 % gesättigte Fettsäure (C8/C10)
- 8 % Mischformal von Fettalkohol C12/C18 + 9 EO mit Butylglycol
- 26 % Kalilauge (38%ig).
- 10 % Kaliumpyrophosphat
- 51% water
- 5% saturated fatty acid (C 8 / C 10 )
- 8% mixed formal of fatty alcohol C 12 / C 18 + 9 EO with butyl glycol
- 26% potassium hydroxide solution (38%).
- 10% potassium pyrophosphate
Man erhält ein klares Mischprodukt mit extrem schwachem Schaumverhalten, welches als 1%ige Lösung ingesetzt wird.A clear mixed product with extremely weak foaming behavior is obtained, which is used as a 1% solution.
Ein alkalisches Reinigungsgranulat zur Entfettung von Metalloberflächen bestehend aus folgender Zusammensetzung:
- 75 % NaOH granuliert
- 19 % Trinatriumphosphat
- 3 % Natrium-tripolyphosphat
- 2 % Natrium-dodecylbenzolsulfonat
- 1 % Mischformal von Oxoalkohol C14/C15 + 11 EO mit Butylglycol
- 75% NaOH granulated
- 19% trisodium phosphate
- 3% sodium tripolyphosphate
- 2% sodium dodecylbenzenesulfonate
- 1% mixed formal of oxo alcohol C 14 / C 15 + 11 EO with butyl glycol
Eine 5%ige Lösung dieses Reinigers zeigt bei 60 bis 90°C ein extrem schwaches Schaumverhalten und sehr gute Entfettungswirkung.A 5% solution of this cleaner shows an extremely weak foaming behavior and very good degreasing effect at 60 to 90 ° C.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT81103326T ATE5328T1 (en) | 1980-05-12 | 1981-05-02 | USE OF ALKYLPOLYGLYCOLE THERMAL FORMALS FOR ANTIFOAM. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803018149 DE3018149A1 (en) | 1980-05-12 | 1980-05-12 | USE OF ALKYLPOLYGLYKOLETHERMAL FORMAL FOR FOAM PREVENTION |
| DE3018149 | 1980-05-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0040713A1 true EP0040713A1 (en) | 1981-12-02 |
| EP0040713B1 EP0040713B1 (en) | 1983-11-16 |
Family
ID=6102215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP81103326A Expired EP0040713B1 (en) | 1980-05-12 | 1981-05-02 | Use of mixed formals of alkylpolyglycol ethers as foam suppressing agents |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4364777A (en) |
| EP (1) | EP0040713B1 (en) |
| JP (1) | JPS5715806A (en) |
| AR (1) | AR223116A1 (en) |
| AT (1) | ATE5328T1 (en) |
| BR (1) | BR8102900A (en) |
| CA (1) | CA1157736A (en) |
| DE (2) | DE3018149A1 (en) |
| DK (1) | DK166781A (en) |
| ES (1) | ES8300018A1 (en) |
| FI (1) | FI66900C (en) |
| MX (1) | MX7094E (en) |
| NO (1) | NO151244C (en) |
| TR (1) | TR21341A (en) |
| ZA (1) | ZA813128B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054894A1 (en) * | 1980-12-23 | 1982-06-30 | Hoechst Aktiengesellschaft | Surfactant-containing mixture for cleaning hard surfaces |
| EP0124815A3 (en) * | 1983-05-02 | 1987-04-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of polyglycol ethers as foam-depressing additives in cleaning agents producing little foam |
| EP0564402A1 (en) * | 1992-04-01 | 1993-10-06 | Ciba-Geigy Ag | Low foaming surfactant compounds |
| WO2015113860A1 (en) * | 2014-01-30 | 2015-08-06 | Basf Se | Asymmetric formales and acetales as adjuvants for crop protection |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394273A (en) * | 1981-12-10 | 1983-07-19 | Nl Industries, Inc. | Defoamers for aqueous liquids containing soluble zinc salts |
| DE3338923C1 (en) * | 1983-10-27 | 1985-02-21 | Th. Goldschmidt Ag, 4300 Essen | Use of copolymers of polyoxyalkylene ethers of allyl and / or methallyl alcohol and vinyl esters as demulsifiers for crude oil containing water |
| DE3345349A1 (en) * | 1983-12-15 | 1985-06-27 | Henkel KGaA, 4000 Düsseldorf | USE OF POLYGLYCOLETHERS AS FOAM-PRESSING ADDITIVES IN LOW-FOAM CLEANERS |
| DE3418523A1 (en) * | 1984-05-18 | 1985-11-21 | Basf Ag, 6700 Ludwigshafen | END-GROUP LOCKED FATTY ALCOHOL ALCOXYLATES FOR INDUSTRIAL CLEANING PROCESSES, ESPECIALLY FOR BOTTLE WASHING AND FOR METAL CLEANING |
| DE3641447A1 (en) * | 1986-12-04 | 1988-06-09 | Henkel Kgaa | TENSIDE MIXTURES AS COLLECTORS FOR THE FLOTATION OF NON-SULFIDIC ORES |
| SE462599B (en) * | 1987-04-06 | 1990-07-23 | Berol Kemi Ab | PRE-PACKING THAT PREVENTS FOAM PREPARATION, PREPARING SUCH PRE-PACKAGING AND ANTI-DUMPING AGENTS |
| KR960001013B1 (en) * | 1987-06-25 | 1996-01-17 | 가오 가부시끼가이샤 | Aqueous composition of strong alkali and nonionic surfactant |
| GB8906820D0 (en) * | 1989-03-23 | 1989-05-10 | Ici Plc | Novel chemical compounds and their use as low foam surfactants and antifoamingagents |
| US5068444A (en) * | 1989-10-31 | 1991-11-26 | Texaco Chemical Company | Tetramines by amination of dialdehyde glycol adducts |
| US5399239A (en) * | 1992-12-18 | 1995-03-21 | Ceridian Corporation | Method of fabricating conductive structures on substrates |
| CN109607648A (en) * | 2018-12-19 | 2019-04-12 | 宁波瑞凌新能源科技有限公司 | A kind of radiation refrigeration formula desalination plant |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1225800B (en) * | 1964-01-11 | 1966-09-29 | Henkel & Cie Gmbh | Low-foaming detergents and cleaning agents |
| DE2523588A1 (en) * | 1975-05-28 | 1976-12-16 | Hoechst Ag | POLYGLYCOL ETHERMAL FORMALS AND THEIR USE AS CORROSIVE WETTING, DETERGENT AND CLEANING AGENTS |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA656004A (en) * | 1963-01-15 | A. Bixler Dean | Detergent composition | |
| US2905719A (en) * | 1959-09-22 | Cxhzo | ||
| US2905718A (en) * | 1957-09-24 | 1959-09-22 | Rohm & Haas | Surface-active acetals and formals |
| US2905720A (en) * | 1957-09-24 | 1959-09-22 | Rohm & Haas | Surface-active acetals and formals |
| US3048548A (en) * | 1959-05-26 | 1962-08-07 | Economics Lab | Defoaming detergent composition |
| BE624833A (en) * | 1962-02-28 | |||
| US4070298A (en) * | 1976-07-26 | 1978-01-24 | Olin Corporation | Defoaming detergent additive |
| DE2812443C2 (en) | 1978-03-22 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Polyglycol ether thermal formals and their use as fiber finishes |
-
1980
- 1980-05-12 DE DE19803018149 patent/DE3018149A1/en not_active Withdrawn
-
1981
- 1981-04-13 FI FI811131A patent/FI66900C/en not_active IP Right Cessation
- 1981-04-13 DK DK166781A patent/DK166781A/en not_active IP Right Cessation
- 1981-04-13 NO NO811284A patent/NO151244C/en unknown
- 1981-04-27 US US06/257,855 patent/US4364777A/en not_active Expired - Fee Related
- 1981-04-30 CA CA000376613A patent/CA1157736A/en not_active Expired
- 1981-05-02 DE DE8181103326T patent/DE3161415D1/en not_active Expired
- 1981-05-02 AT AT81103326T patent/ATE5328T1/en not_active IP Right Cessation
- 1981-05-02 EP EP81103326A patent/EP0040713B1/en not_active Expired
- 1981-05-08 MX MX819442U patent/MX7094E/en unknown
- 1981-05-11 ES ES502104A patent/ES8300018A1/en not_active Expired
- 1981-05-11 BR BR8102900A patent/BR8102900A/en unknown
- 1981-05-11 ZA ZA00813128A patent/ZA813128B/en unknown
- 1981-05-12 AR AR285290A patent/AR223116A1/en active
- 1981-05-12 TR TR21341A patent/TR21341A/en unknown
- 1981-05-12 JP JP7287381A patent/JPS5715806A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1225800B (en) * | 1964-01-11 | 1966-09-29 | Henkel & Cie Gmbh | Low-foaming detergents and cleaning agents |
| DE2523588A1 (en) * | 1975-05-28 | 1976-12-16 | Hoechst Ag | POLYGLYCOL ETHERMAL FORMALS AND THEIR USE AS CORROSIVE WETTING, DETERGENT AND CLEANING AGENTS |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054894A1 (en) * | 1980-12-23 | 1982-06-30 | Hoechst Aktiengesellschaft | Surfactant-containing mixture for cleaning hard surfaces |
| EP0124815A3 (en) * | 1983-05-02 | 1987-04-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of polyglycol ethers as foam-depressing additives in cleaning agents producing little foam |
| EP0564402A1 (en) * | 1992-04-01 | 1993-10-06 | Ciba-Geigy Ag | Low foaming surfactant compounds |
| CH684933A5 (en) * | 1992-04-01 | 1995-02-15 | Ciba Geigy Ag | Low foaming surfactants. |
| WO2015113860A1 (en) * | 2014-01-30 | 2015-08-06 | Basf Se | Asymmetric formales and acetales as adjuvants for crop protection |
| CN105939602A (en) * | 2014-01-30 | 2016-09-14 | 巴斯夫欧洲公司 | Asymmetric formales and acetales as adjuvants for crop protection |
| AU2015213032B2 (en) * | 2014-01-30 | 2018-11-01 | Basf Se | Asymmetric formales and acetales as adjuvants for crop protection |
| CN105939602B (en) * | 2014-01-30 | 2020-01-14 | 巴斯夫欧洲公司 | Asymmetric formals and acetals as adjuvants in crop protection |
| US11051510B2 (en) | 2014-01-30 | 2021-07-06 | Basf Se | Asymmetric formales and acetales as adjuvants for crop protection |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3161415D1 (en) | 1983-12-22 |
| AR223116A1 (en) | 1981-07-15 |
| ES502104A0 (en) | 1982-10-01 |
| NO151244C (en) | 1985-03-06 |
| FI66900C (en) | 1984-12-10 |
| FI811131L (en) | 1981-11-13 |
| CA1157736A (en) | 1983-11-29 |
| ES8300018A1 (en) | 1982-10-01 |
| JPS5715806A (en) | 1982-01-27 |
| DE3018149A1 (en) | 1981-11-19 |
| TR21341A (en) | 1984-04-16 |
| FI66900B (en) | 1984-08-31 |
| ATE5328T1 (en) | 1983-12-15 |
| EP0040713B1 (en) | 1983-11-16 |
| DK166781A (en) | 1981-11-13 |
| MX7094E (en) | 1987-06-08 |
| NO151244B (en) | 1984-11-26 |
| BR8102900A (en) | 1982-02-02 |
| ZA813128B (en) | 1982-05-26 |
| NO811284L (en) | 1981-11-13 |
| US4364777A (en) | 1982-12-21 |
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