EP0421146A2 - Drying agent for painted surfaces - Google Patents
Drying agent for painted surfaces Download PDFInfo
- Publication number
- EP0421146A2 EP0421146A2 EP90117245A EP90117245A EP0421146A2 EP 0421146 A2 EP0421146 A2 EP 0421146A2 EP 90117245 A EP90117245 A EP 90117245A EP 90117245 A EP90117245 A EP 90117245A EP 0421146 A2 EP0421146 A2 EP 0421146A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oily component
- drying agent
- agent according
- 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.)
- Withdrawn
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- 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
- C11D3/43—Solvents
-
- 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
- C11D1/40—Monoamines or polyamines; Salts thereof
-
- 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
- C11D1/667—Neutral esters, e.g. sorbitan esters
Definitions
- Cationic surfactants suitable for formulations in drying agents for paint surfaces are described in detail in DE-OS 28 06 980 and 30 32 220 and in Polishing and waxing compositions, MG Halpern, Noyes Data Corporation, USA (1982), pp. 78-89).
Abstract
Description
Die Erfindung betrifft ein neues, leicht biologisch abbaubares Trocknungsmittel für Autowaschanlagen. Solche Mittel werden dem Wasser des letzten Spülgangs in Autowaschanlagen in geringen Mengen zugegeben. Die Wirkbestandteile wandern dabei aus dem Wasser auf die Lackoberfläche und bilden dadurch eine hydrophobierende Schicht, die den Wasserfilm aufreißen läßt, so daß ein Großteil des Wassers von allein abtropft.The invention relates to a new, easily biodegradable drying agent for car washes. Such agents are added to the water of the last rinse in car washes in small quantities. The active ingredients migrate from the water to the surface of the paint and thereby form a hydrophobizing layer that allows the water film to tear, so that a large part of the water drips off by itself.
Solche Trocknungsmittel, bzw. Hydrophobierungsmittel enthalten kationische Tenside und eine ölige Komponente als Wirksubstanzen, sowie als Hilfsbestandteile Emulgatoren und Lösungsvermittler. Emulgatoren und Lösungsvermittler werden benötigt, um aus den Wirksubstanzen ein einheitliches, wasserverdünnbares und dadurch in der Praxis verwendbares Produkt herstellen zu können. Als Konservierungsmittel enthalten solche Produkte zusätzlich noch Wachse oder Silicone, um eine längere Haltbarkeit dieser Hydrophobierungsschicht zu bewirken.Such drying agents or water repellents contain cationic surfactants and an oily component as active substances, and as auxiliary components, emulsifiers and solubilizers. Emulsifiers and solubilizers are required in order to be able to produce a uniform, water-dilutable product that can be used in practice from the active substances. Such products also contain waxes or silicones as preservatives in order to ensure that this hydrophobic layer lasts longer.
Marktübliche Trocknungsmittel enthalten Kohlenwasserstoffe, wie Alkylbenzole, Mineralöle oder Petroleum, als ölige Komponente und eventuell als Lösungsmittel. Diese zeigen zwar eine sehr gute Hydrophobierungswirkung, sind aber im Wasser nur schwer abbaubar.Commercial drying agents contain hydrocarbons, such as alkylbenzenes, mineral oils or petroleum, as an oily component and possibly as a solvent. Although these show a very good hydrophobic effect, they are difficult to degrade in water.
Es wurde versucht, kohlenwasserstofffreie Trocknungsmittel herzustellen. Ohne die ölige Komponente ist die Trocknungswirkung jedoch zu schlecht.Attempts have been made to produce hydrocarbon-free drying agents. Without the oily component, however, the drying effect is too poor.
In der DE-OS 34 27 726 wird die Verwendung eines speziellen Acetals als ölige Komponente beschrieben. Diese Acetale lassen sich aber nicht mit den neueren, besonders leicht biologisch abbaubaren, kationischen Tensiden der Struktur (XIV) kombinieren, da sie nur im sauren Bereich (unter PH 6) ausreichend lagestabil sind und die Acetate nur im alkalischen Bereich stabil (Hans Bayer, Lehrbuch der org. Chemie, S. Hirzel Verlag, Stuttgart (1973) S. 178) sind.DE-OS 34 27 726 describes the use of a special acetal as an oily component. However, these acetals cannot be combined with the newer, particularly readily biodegradable, cationic surfactants of the structure (XIV), since they are only sufficiently stable in the acidic range (below PH 6) and the acetates are only stable in the alkaline range (Hans Bayer, Textbook of the org.Chemistry, S. Hirzel Verlag, Stuttgart (1973) p. 178).
In der DE-OS 28 06 980 werden C₈-C₂₀-Alkohole als ölige Komponente vorgeschlagen. Diese Art von kohlenwasserstofffreiem Trockner zeigte in eigenen Versuchen kein zufriedenstellendes Ergebnis.In DE-OS 28 06 980 C₈-C₂₀ alcohols are proposed as an oily component. This type of hydrocarbon-free dryer has not shown a satisfactory result in its own experiments.
Es hat sich überraschender Weise herausgestellt, daß Substanzen der allgemeinen Formel R₁ - X - R₂ als ölige Komponente für Trocknungsmittel von Lackoberflächen geeignet sind.It has surprisingly been found that substances of the general formula R₁ - X - R₂ are suitable as an oily component for drying agents on paint surfaces.
In der allgemeinen Formel sind R₁ und R₂ Alkyl- oder Alkenylreste mit 6 bis 18 Kohlenstoffatomen und X eine der Gruppierungen:
Beispiele für Ester als ölige Komponente der allgemeinen Formel (I) in der X die Bedeutung der Formel (II) hat, sind z.B. Fettalkohol(C₁₀-C₁₂)-isooktansäureester, Oktyl-fettsäure(C₈-C₁₂)ester, Fettsäure(C₁₂-C₆)hexylester, Fettsäure(C₁₂-C₆)-cyclohexylester, Fettsäure(C₈-C₁₀)-decylester, Alkyl(C₁₂-C₁₈)-capronsäureester.
Beispiele einer öligen Komponente der allgemeinen Formel (I), in der X den Rest (III) bedeutet, d.h. von tertiären Aminen, sind beispielsweise Trioktylamin, Trihexylamin, Didecyl-methyl-amin, Alkyl(C₁₂-C₁₄)morpholin, Alkyl(C₁₂-C₁₆)-piperidin.
Amide als ölige Komponente der allgemeinen Formel (I), in der X die Bedeutung der Formel (IV) hat, sind beispielsweise Ethylcapronsäure-dioktylamid, Fettsäure(C₁₀-C₁₈)- piperidinamid, Ethylcaprosäure-alkyl(C₈-C₁₂)amid.Examples of esters as an oily component of the general formula (I) in which X has the meaning of the formula (II) are, for example, fatty alcohol (C₁₀-C₁₂) isooctanoate, octyl fatty acid (C₈-C₁₂) ester, fatty acid (C₁₂-C₆ ) hexyl ester, fatty acid (C₁₂-C₆) cyclohexyl ester, fatty acid (C₈-C₁₀) decyl ester, alkyl (C₁₂-C₁₈) caproic acid ester.
Examples of an oily component of the general formula (I) in which X is the radical (III), ie of tertiary amines, are, for example, trioctylamine, trihexylamine, didecylmethylamine, alkyl (C₁₂-C₁₄) morpholine, alkyl (C₁₂- C₁₆) piperidine.
Amides as an oily component of the general formula (I) in which X has the meaning of the formula (IV) are, for example, ethylcaproic acid dioctylamide, fatty acid (C₁₀-C₁₈) piperidinamide, ethylcaproic acid alkyl (C₈-C₁₂) amide.
Beispiele geeigneter Ether nach den allgemeinen Formeln (I) und (V) sind der Di(C₈-C₁₂)-alkylether, Dioktylether, Didecylether.
Ester von Dicarbonsäuren als ölige Komponente nach den allgemeinen Formeln (I) und (VI) sind beispielsweise Dioktylmaleinat, Dioktylfumarat, Di(C₈-C₁₂)alkyltrimethyladipate, Bernsteinsäure-diisooktylester, Oxalsäure-didecylester, Oxalsäure-diisooktylester.Examples of suitable ethers according to the general formulas (I) and (V) are the di (C₈-C₁₂) alkyl ether, dioctyl ether, didecyl ether.
Esters of dicarboxylic acids as an oily component according to the general formulas (I) and (VI) are, for example, dioctyl maleate, dioctyl fumarate, di (C₈-C₁₂) alkyl trimethyl adipate, succinic acid diisooctyl ester, oxalic acid didecyl ester, oxalic acid diisooctyl ester.
Verbindungen nach der allgemeinen Formel (I), in der X die Bedeutung der Formel (VII) hat, sind beispielsweise Dialkyl(C₈-C₁₂)mono- oder -dialkylenglykole, Ethylenglykol-diisooktylether, Diethylenglykol-diisooktylether.Compounds of the general formula (I) in which X has the meaning of the formula (VII) are, for example, dialkyl (C₈-C₁₂) mono- or dialkylene glycols, ethylene glycol diisooctyl ether, diethylene glycol diisooctyl ether.
Beispiele von Verbindungen der Formeln (I) und (VIII) sind Tetrabutyl-ethylendiamin und Tetraisooktyl-ethylendiamin.Examples of compounds of formulas (I) and (VIII) are tetrabutyl-ethylenediamine and tetraisooctyl-ethylenediamine.
Als Beispiel einer Verbindung der allgemeinen Formel (I), in der X die Bedeutung der Formel (IX) hat, wäre Isooktylmaleinsäure-alkyl(C₈-C₁₀)amid zu nennen.As an example of a compound of general formula (I) in which X has the meaning of formula (IX), alkyl isooctyl maleic acid (C₈-C₁₀) amide should be mentioned.
Ölige Komponenten nach den allgemeinen Formeln (I) und (X) sind Di-N,N′-dicyl-maleinsäurediamid und Di-N,N′-(methyl-decyl)-maleinsäurediamid.Oily components according to the general formulas (I) and (X) are di-N, N'-dicyl-maleic acid diamide and di-N, N '- (methyl-decyl) -maleic acid diamide.
Als weitere Inhaltsstoffgruppen enthalten die Trocknungsmittel:
- 1) Ein kationisches Tensid bzw. Tensidgemisch
- 2) Einen Emulgator bzw. Emulgatorgemisch
- 3) Ein Lösungsmittel bzw. Lösungsmittelgemisch
- 4) Konservierungsmittel, wie Wachse und Silicone
- 1) A cationic surfactant or surfactant mixture
- 2) An emulsifier or mixture of emulsifiers
- 3) A solvent or solvent mixture
- 4) Preservatives such as waxes and silicones
Für Formulierungen in Trocknungsmitteln für Lackoberflächen geeignete kationische Tenside sind ausführlich beschrieben in den DE-OS 28 06 980 und 30 32 220 sowie in Polishing and waxing compositions, M. G. Halpern, Noyes Data Corporation, USA (1982), S.78-89).Cationic surfactants suitable for formulations in drying agents for paint surfaces are described in detail in DE-OS 28 06 980 and 30 32 220 and in Polishing and waxing compositions, MG Halpern, Noyes Data Corporation, USA (1982), pp. 78-89).
Bei den quaternären Ammoniumverbindungen als kationisches Tensid handelt es sich in der Regel um Substanzen der Strukturformeln (XVIII bis XXI) mit ein bis drei langen Alkylresten. Die langen Alkylreste sind in der Regel Oleyl- oder Stearyl-Reste bzw. Reste der natürlichen Mischungen des Talgfetts, Kokosöls oder des Sojaöls.
In den allgemeinen Formeln (XVIII bis XXI) hat Y die Bedeutung Cl, Br, J, Phosphat, Methosulfat, Acetat, Propionat, Benzoat.In the general formulas (XVIII to XXI), Y has the meaning Cl, Br, J, phosphate, methosulfate, acetate, propionate, benzoate.
Geeignete Emulgatoren sind gleichfalls in den oben genannten Druckschriften beschrieben. Es handelt sich beispielsweise um Alkyl-(Alkylen)amine, Alkyl-(Alkylen-)diamine, Alkyl-(Alkylen-)amin-polyethylenglykoladdukte, Alkyl-(Alkylen-)amin-polypropylenglykoladdukte, Alkyl-(Alkylen-)alkohol-polyethylenglykole.Suitable emulsifiers are also described in the publications mentioned above. Examples include alkyl (alkylene) amines, alkyl (alkylene) diamines, alkyl (alkylene) amine-polyethylene glycol adducts, alkyl (alkylene) amine-polypropylene glycol adducts, alkyl (alkylene) alcohol-polyethylene glycols.
Für die Zwecke der Erfindung werden bevorzugt Kokosfettamin, N-Oleyl-1,3-diaminopropan, N-Talgfett-1,3-diaminopropan, Sojaölamin, Stearylamin, Oleylamin, Alkylalkohol(C₁₀-C₁₈)-polyethylenglykoladdukte.For the purposes of the invention, preference is given to coconut fatty amine, N-oleyl-1,3-diaminopropane, N-tallow fat-1,3-diaminopropane, soybean oil amine, stearylamine, oleylamine, alkyl alcohol (C₁₀-C₁₈) polyethylene glycol adducts.
Geeignete Lösungsvermittler sind gleichfalls in den genannten Literaturstellen beschrieben.Suitable solubilizers are also described in the references mentioned.
Für die Zwecke der Erfindung sind vorzugsweise niedere Alkohole wie Methanol, Ethanol, Isopropanol, n-Propanol, sec. Butanol, Ethylenglykol, Diethylenglykol, Ethylglykol, Butylglykol, Butyldiglykol sowie cyclische Polydimethylsiloxane geeignet.Lower alcohols such as methanol, ethanol, isopropanol, n-propanol, sec. Butanol, ethylene glycol, diethylene glycol, ethyl glycol, butyl glycol, butyl diglycol and cyclic polydimethylsiloxanes are preferably suitable for the purposes of the invention.
Besonders bevorzugt werden Diethylenglykoldimethylether und N-(2-hydroxyalkyl)-acetamide.Diethylene glycol dimethyl ether and N- (2-hydroxyalkyl) acetamides are particularly preferred.
Für die Zwecke der Erfindung geeignete Konservierungsmittel wie Wachsemulsionen und aminofunktionelle Silicone sind in der oben erwähnten Literaturstelle Polishing and waxing compositions ... sowie auf Seite 117 im Jahrbuch für den Praktiker 1988 von B. ZIOLKOWSKY, Verlag für Chemische Industrie H. Ziolkowsky KG, Augsburg, beschrieben.Preservatives suitable for the purposes of the invention, such as wax emulsions and amino-functional silicones, can be found in the above-mentioned reference Polishing and waxing compositions ... and on page 117 in the yearbook for practitioners 1988 by B. ZIOLKOWSKY, publisher for chemical industry H. Ziolkowsky KG, Augsburg , described.
In dem erfindungsgemäßen Trocknungsmittel liegen die einzelnen Komponenten vorzugsweise in folgenden Mengen vor:
In der Handelsform liegen die Trocknungsmittel in der Regel schon mit Wasser verdünnt vor.In the commercial form, the drying agents are usually already diluted with water.
32 Gew.% Mischung aus: Di(talg)dimethylammoniumchlorid (Strukturformel XVIII) Alkylimidazolinium-methosulfat (Strukturformel XIX)
12 Gew.% Mischung aus: Dimethylkokosfettamin Dimethylsojaölamin
22 Gew.% Mischung aus: Alkyl(C₈-C₁₄)carbonsäure-alkyl(C₈-C₁₄)ester
30 Gew.% Mischung aus: Dekamethylpentasiloxan Diethylenglykoldimethylether
4 Gew.% Essigsäure32% by weight mixture of: di (tallow) dimethylammonium chloride (structural formula XVIII) alkylimidazolinium methosulfate (structural formula XIX)
12% by weight mixture of: dimethyl coconut fatty amine dimethyl soy oil amine
22 wt.% Mixture of: alkyl (C₈-C₁₄) carboxylic acid alkyl (C₈-C₁₄) ester
30% by weight mixture of: decamethylpentasiloxane diethylene glycol dimethyl ether
4% by weight of acetic acid
Die Essigsäure wandelt die als Emulgatoren eingesetzten Amine in die entsprechenden Ammoniumacetate um und bewirkt, daß das Trocknungsmittel in der mit Wasser verdünnten Form leicht sauer eingestellt wird.The acetic acid converts the amines used as emulsifiers into the corresponding ammonium acetates and has the effect that the drying agent is made slightly acidic in the form diluted with water.
28,5 Gew.% Mischung aus: Di-fettsäure-isoproyplesterdimethylammonium-methosulfat Fettsäure-ethylester-di-(methoxyethyl)-methylammonium-methosulfat (Struktur XXI)
10,0 Gew.% Mischung aus: N-Alkyl(C₁₆-C₁₈)1,3-diaminopropan und/oder N-Alkylen (C₁₆-C₁₈)-1,3-Diaminopropan
22,0 Gew.% Mischung aus: Alkyl (C₈-C₁₄)-carbonsäurealkyl (C₈-C₁₄)-ester
33,5 Gew.% Mischung aus: Dekamethylpentasiloxan Diethylenglykoldimethylether N-(2-hydroxyalkyl)-acetamide
6,0 Gew.% Propionsäure28.5% by weight mixture of: di-fatty acid isoproyplesterdimethylammonium methosulfate fatty acid ethyl ester di (methoxyethyl) methylammonium methosulfate (structure XXI)
10.0 wt.% Mixture of: N-alkyl (C₁₆-C₁₈) 1,3-diaminopropane and / or N-alkylene (C₁₆-C₁₈) -1,3-diaminopropane
22.0 wt.% Mixture of: alkyl (C₈-C₁₄) carboxylic acid alkyl (C₈-C₁₄) ester
33.5% by weight mixture of: decamethylpentasiloxane diethylene glycol dimethyl ether N- (2-hydroxyalkyl) -acetamide
6.0% by weight propionic acid
Entsprechend Beispiel 1 werden durch die Propionsäure aus den als Emulgatoren eingesetzten Aminen die entsprechenden Ammoniumpropionate gebildet und das mit Wasser vorverdünnte Trocknungsmittel schwach sauer eingestellt.According to Example 1, the corresponding ammonium propionates are formed from the amines used as emulsifiers and the drying agent prediluted with water is made slightly acidic by the propionic acid.
Claims (11)
R₁ - X - R₂ (I)
hat, in der R₁ und R₂ Alkyl- oder Alkenylreste mit 6 bis 18 Kohlenstoffatomen in der Kette und X eine der Gruppierungen
R₁ - X - R₂ (I)
has in the R₁ and R₂ alkyl or alkenyl radicals having 6 to 18 carbon atoms in the chain and X one of the groupings
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19893932004 DE3932004A1 (en) | 1989-09-26 | 1989-09-26 | DRYING AGENT FOR PAINT SURFACES |
DE3932004 | 1989-09-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0421146A2 true EP0421146A2 (en) | 1991-04-10 |
EP0421146A3 EP0421146A3 (en) | 1992-09-09 |
Family
ID=6390167
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19900117245 Withdrawn EP0421146A3 (en) | 1989-09-26 | 1990-09-07 | Drying agent for painted surfaces |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0421146A3 (en) |
DE (1) | DE3932004A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021743A1 (en) * | 1991-05-31 | 1992-12-10 | Exxon Chemical Patents Inc. | Rinsing composition |
EP0726931A1 (en) * | 1993-09-29 | 1996-08-21 | Tomah Products, Inc. | Non-toxic biodegradable emulsion compositions for use in automatic car washes |
EP0703291A3 (en) * | 1994-08-30 | 1996-08-21 | Hoechst Ag | Car polish and drying agent |
US5827451A (en) * | 1993-03-17 | 1998-10-27 | Witco Corporation | Microemulsion useful as rinse aid |
WO2009099618A1 (en) * | 2008-02-08 | 2009-08-13 | Evonik Goldschmidt Corp. | Rinse aid compositions with improved characteristics |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
US8569224B2 (en) | 2010-04-01 | 2013-10-29 | Evonik Degussa Gmbh | Fabric softener active composition |
US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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GB1129636A (en) * | 1965-04-14 | 1968-10-09 | Armour & Co | Protective polish |
US3440063A (en) * | 1965-09-30 | 1969-04-22 | Procter & Gamble | Emulsion composition and process for use in automatic car washes |
US3520820A (en) * | 1964-10-30 | 1970-07-21 | Grace W R & Co | Cold water dispersible emulsions of filming amines |
EP0173376A1 (en) * | 1984-07-27 | 1986-03-05 | Rütgerswerke Aktiengesellschaft | Process for drying cars and agent therefor |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2423893B2 (en) * | 1974-05-16 | 1979-04-12 | Chemische Werke Huels Ag, 4370 Marl | Deicing and anti-icing preparations for aircraft surfaces |
DE2806980A1 (en) * | 1978-02-18 | 1979-08-30 | Hoechst Ag | CAR SHINE DRYING AGENT |
-
1989
- 1989-09-26 DE DE19893932004 patent/DE3932004A1/en not_active Withdrawn
-
1990
- 1990-09-07 EP EP19900117245 patent/EP0421146A3/en not_active Withdrawn
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US3520820A (en) * | 1964-10-30 | 1970-07-21 | Grace W R & Co | Cold water dispersible emulsions of filming amines |
GB1129636A (en) * | 1965-04-14 | 1968-10-09 | Armour & Co | Protective polish |
US3440063A (en) * | 1965-09-30 | 1969-04-22 | Procter & Gamble | Emulsion composition and process for use in automatic car washes |
EP0173376A1 (en) * | 1984-07-27 | 1986-03-05 | Rütgerswerke Aktiengesellschaft | Process for drying cars and agent therefor |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992021743A1 (en) * | 1991-05-31 | 1992-12-10 | Exxon Chemical Patents Inc. | Rinsing composition |
US5827451A (en) * | 1993-03-17 | 1998-10-27 | Witco Corporation | Microemulsion useful as rinse aid |
EP0726931A1 (en) * | 1993-09-29 | 1996-08-21 | Tomah Products, Inc. | Non-toxic biodegradable emulsion compositions for use in automatic car washes |
EP0726931A4 (en) * | 1993-09-29 | 1999-04-14 | Tomah Products Inc | Non-toxic biodegradable emulsion compositions for use in automatic car washes |
EP0703291A3 (en) * | 1994-08-30 | 1996-08-21 | Hoechst Ag | Car polish and drying agent |
US5703029A (en) * | 1994-08-30 | 1997-12-30 | Hoechst Aktiengesellschaft | Car dry-bright composition |
WO2009099618A1 (en) * | 2008-02-08 | 2009-08-13 | Evonik Goldschmidt Corp. | Rinse aid compositions with improved characteristics |
US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
US8569224B2 (en) | 2010-04-01 | 2013-10-29 | Evonik Degussa Gmbh | Fabric softener active composition |
US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
Also Published As
Publication number | Publication date |
---|---|
DE3932004A1 (en) | 1991-04-04 |
EP0421146A3 (en) | 1992-09-09 |
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