WO1995023203A1 - Use of glyconic-acid amides as surfactants for cleaning and rinsing hard surfaces - Google Patents

Use of glyconic-acid amides as surfactants for cleaning and rinsing hard surfaces Download PDF

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Publication number
WO1995023203A1
WO1995023203A1 PCT/EP1995/000568 EP9500568W WO9523203A1 WO 1995023203 A1 WO1995023203 A1 WO 1995023203A1 EP 9500568 W EP9500568 W EP 9500568W WO 9523203 A1 WO9523203 A1 WO 9523203A1
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weight
salt
acid
sulfate
cleaning
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PCT/EP1995/000568
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German (de)
French (fr)
Inventor
Udo Hees
Manfred Weuthen
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Henkel Kommanditgesellschaft Auf Aktien
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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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the invention relates to the use of gluconic acid amides as surface-active substances in cleaning and rinsing agents for cleaning and rinsing hard surfaces.
  • Detergents and detergents usually consist of aqueous solutions of synthetic, anionic and / or nonionic surfactants and conventional additives. Cleaning agents are especially used to clean hard surfaces such. B. of glass, painted and polished surfaces, ceramic materials, PVC, linoleum, etc. used. Another important area of application for detergents is the manual washing of dishes and cookware.
  • Alkylbenzenesulfonates, ⁇ -olefin sulfonates, fatty alkyl sulfates and fatty alkyl ether sulfates are usually used as anionic surfactants.
  • the present invention relates to the use of a certain class of nonionic surfactants, the gluconic amides, as surface-active substances in cleaning and rinsing agents for cleaning and rinsing hard surfaces.
  • Gluconic amides can be obtained by reacting amines with gluconic acid lactone or other reactive gluconic acid derivatives. The synthesis is e.g. in US 2,752,334. These substances are surfactants based on renewable raw materials.
  • the invention relates to the use of gluconic amides of the formula I. in which R 1 and R 2 independently represent hydrogen or methyl groups, n and m independently represent zero or integers from 1 to 18, R 3 represents hydrogen, a methyl or an ethyl group and R 4 represents a linear or branched, saturated or unsaturated C 6 -C 22 alkyl group as surface-active substances in dishwashing detergents for cleaning and cleaning hard surfaces.
  • the radical R 4 in formula (I) can be derived from linear or branched, saturated or unsaturated alcohols having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds.
  • Typical representatives are capronic alcohol, caprylic alcohol, capric alcohol, myristyl alcohol, lauryl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol or erucyl alcohol.
  • the radical R 4 preferably consists of 12 to 18 carbon atoms.
  • R 3 is preferably hydrogen and n and m are preferably zero. If, however, a better water solubility of the gluconic acid amides is to be achieved, then n and / or m are not equal to zero, ethoxylated products are then preferably present, ie R 1 and R 2 are each hydrogen.
  • the cleaning and rinsing agents contain the gluconic acid amides of the formula I in an amount of 0.1 to 50% by weight, based on the total agent.
  • Anionic surfactants are preferably additionally contained, e.g. B.
  • nonionic surfactants can also be present in an amount of 0.1 to 40% by weight, based on the total agent.
  • Suitable nonionic surfactants are, for. B. alkyl or alkenyl oligoglycosides of the formula R 5 O- [Z] x , in which R5 is an alkyl or alkenyl radical having 8-22 carbon atoms, Z is a sugar radical having 5 or 6 carbon atoms, in particular a glucose radical, and x represents numbers from 1 to 10, C 8 -C 18 fatty acid mono- and diC 1 -C 4 alkanolamides, C 8 -C 18 fatty acid glucamides, adducts of ethylene oxide and / or propylene oxide with C 8 -C 18 - Fatty alcohols and on mono- and di-C 8 -C 18 fatty acid glycerides.
  • the cleaning agents according to the invention can contain additional surface-active substances, e.g. B. betaine surfactants or fatty amine oxides.
  • additional surface-active substances e.g. B. betaine surfactants or fatty amine oxides.
  • B. betaine surfactants or fatty amine oxides may also optionally be included; these substances are builders, e.g. B. glutaric acid, succinic acid, adipic acid, tartaric acid, benzene hexacarboxylic acid, gluconic acid, trisodium citrate; Solvents such as ethanol; Hydrotropes, e.g. B.
  • Viscosity regulators for example synthetic polymers such as polyacrylates
  • pH regulators for example citric acid, triethanolamine or NaOH
  • Preservatives eg glutaraldehyde
  • Dyes and fragrances as well as opacifiers or skin protection agents as described in EP-A-522 756.
  • the following examples are intended to explain the subject in more detail, but without restricting it thereto.
  • the pH of the detergent formulations can be varied over a wide range, since the gluconic amides are hydrolysis-stable over a wide range, but a pH range from 5.5 to 9.5 is preferred.
  • all formulations can contain the components typically used in general-purpose cleaners, such as builders, perfume, dyes or thickeners, or the components typically used in manual dishwashing detergents, such as perfumes, dyes, opacifiers, thickeners or skin protection components.
  • the pH of the formulations is generally between 5.5 and 9.5, but pH values outside this range are also possible.
  • NRE Narrow ranks ethoxylate (ethoxylate with restricted
  • APG 225 C 8/10 alkyl polyglucoside with a DP of 1.6
  • polyethylene oxide MW 600000

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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)

Abstract

The glyconic-acid amides described are suitable for use as surface-active agents in the cleaning and rinsing of hard surfaces, particularly in combination with the usual anionic and non-ionic surfactants.

Description

"Verwendung von Gluconsäureamiden als Tenside zum Reinigen und Spülen harter Oberflächen"  "Use of gluconic acid amides as surfactants for cleaning and rinsing hard surfaces"
Gegenstand der Erfindung ist die Verwendung von Gluconsäureamiden als oberflächenaktive Substanzen in Reinigungs- und Spülmitteln zum Reinigen und Spülen harter Oberflächen. The invention relates to the use of gluconic acid amides as surface-active substances in cleaning and rinsing agents for cleaning and rinsing hard surfaces.
Reinigungs- und Spülmittel bestehen meist aus wäßrigen Lösungen von synthetischen, anionischen und/oder nichtionischen Tensiden und üblichen Zusatzstoffen. Reinigungsmittel werden besonders zum Reinigen harter Oberflächen z. B. von Glas, lackierten und polierten Oberflächen, keramischen Materialien, PVC, Linoleum etc. verwendet. Ein weiteres wichtiges Anwendungsgebiet für Spülmittel ist das manuelle Spülen von Eß- und Kochgeschirr. Detergents and detergents usually consist of aqueous solutions of synthetic, anionic and / or nonionic surfactants and conventional additives. Cleaning agents are especially used to clean hard surfaces such. B. of glass, painted and polished surfaces, ceramic materials, PVC, linoleum, etc. used. Another important area of application for detergents is the manual washing of dishes and cookware.
Als Aniontenside werden dabei üblicherweise Alkylbenzolsulfonate, α-Olefinsulfonate, Fettalkylsulfate und Fettalkylethersulfate, eingesetzt. Alkylbenzenesulfonates, α-olefin sulfonates, fatty alkyl sulfates and fatty alkyl ether sulfates are usually used as anionic surfactants.
Die vorliegende Erfindung betrifft die Verwendung einer bestimmten Klasse nichtionischer Tenside, der Gluconsäureamide, als oberflächenaktive Substanzen in Reinigungs- und Spülmitteln zum Reinigen und Spülen harter Oberflächen. Gluconsäureamide sind zugänglich durch Umsetzung von Aminen mit Gluconsäurelacton oder anderen reaktiven Gluconsäurederivaten. Die Synthese ist z.B. in US 2,752,334 beschrieben. Diese Substanzen stellen Tenside auf Basis nachwachsender Rohstoffe dar. The present invention relates to the use of a certain class of nonionic surfactants, the gluconic amides, as surface-active substances in cleaning and rinsing agents for cleaning and rinsing hard surfaces. Gluconic amides can be obtained by reacting amines with gluconic acid lactone or other reactive gluconic acid derivatives. The synthesis is e.g. in US 2,752,334. These substances are surfactants based on renewable raw materials.
Gegenstand der Erfindung ist die Verwendung von Gluconsäureamiden der Formel I
Figure imgf000004_0001
in der R1 und R2 unabhängig voneinander Wasserstoffe oder Methylgruppen bedeuten, n und m unabhängig voneinander Null oder ganze Zahlen von 1 bis 18 darstellen, R3 Wasserstoff, eine Methyl- oder eine Ethylgruppe darstellt und R4 für eine lineare oder verzweigte, gesättigte oder ungesättigte C6-C22-Alkylgruppe steht, als oberflächenaktive Substanzen in Spülund Reinigungsmitteln zum Spülen und Reinigen harter Oberflächen. The invention relates to the use of gluconic amides of the formula I.
Figure imgf000004_0001
in which R 1 and R 2 independently represent hydrogen or methyl groups, n and m independently represent zero or integers from 1 to 18, R 3 represents hydrogen, a methyl or an ethyl group and R 4 represents a linear or branched, saturated or unsaturated C 6 -C 22 alkyl group as surface-active substances in dishwashing detergents for cleaning and cleaning hard surfaces.
Der Rest R4 in Formel (I) kann sich von linearen oder verzweigten, gesättigten oder ungesättigten Alkoholen mit 6 bis 22 Kohlenstoffatomen und 0, 1, 2 oder 3 Doppelbindungen ableiten. Typische Vertreter sind Capronalkohol, Caprylalkohol, Caprinalkohol, Myristylalkohol, Laurylalkohol, Cetylalkohol, Palmitoleylalkohol, Stearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselylalkohol, Linolylalkohol, Linolenylalkohol, Behenylalkohol oder Erucylalkohol. The radical R 4 in formula (I) can be derived from linear or branched, saturated or unsaturated alcohols having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds. Typical representatives are capronic alcohol, caprylic alcohol, capric alcohol, myristyl alcohol, lauryl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol or erucyl alcohol.
Vorzugsweise besteht der Rest R4 aus 12 bis 18 C-Atomen. R3 steht vorzugsweise für Wasserstoff und n und m sind vorzugsweise Null. Soll jedoch eine bessere Wasserlöslichkeit der Gluconsäureamide erzielt werden, dann sind n und/oder m ungleich Null, vorzugsweise liegen dann ethoxylierte Produkte vor, d. h. R1 und R2 sind jeweils Wasserstoffe. Die Gluconsäureamide der Formel I sind in den Reinigungs- und Spülmitteln in einer Menge von 0,1 bis 50 Gew.-%, bezogen auf das gesamte Mittel, enthalten. Vorzugsweise sind zusätzlich Aniontenside enthalten, z. B. C8-C18-Alkylsulfate, C8-C18-Alkylethersulfate, C8-C18-Alkansulfonate, C8-C18-α-Olefinsulfonate, sulfonierte C8-C18-Fettsäuren, C1-C4-Alkylester, C6-C18-Alkylbenzolsulfonate, Sulfonbernsteinsäuremono- und -di-C1-C12-Alkylester, C8-C18-Alkylpolyglykolethercarboxylate, C8-C18-N-Acyltauride, C8-C18-N-Sarkosinate oder C8-C18-Alkylisethionate, die ebenfalls in einer Menge von 0,1 bis 50 Gew.-%, bezogen auf das gesamte Mittel, enthalten sein können. Für alle Aniontenside gilt, daß sie im allgemeinen in Form ihrer Ammonium-, Alkanolammonium-, Alkali- oder Magnesiumsalze vorliegen. The radical R 4 preferably consists of 12 to 18 carbon atoms. R 3 is preferably hydrogen and n and m are preferably zero. If, however, a better water solubility of the gluconic acid amides is to be achieved, then n and / or m are not equal to zero, ethoxylated products are then preferably present, ie R 1 and R 2 are each hydrogen. The cleaning and rinsing agents contain the gluconic acid amides of the formula I in an amount of 0.1 to 50% by weight, based on the total agent. Anionic surfactants are preferably additionally contained, e.g. B. C 8 -C 18 alkyl sulfates, C 8 -C 18 alkyl ether sulfates, C 8 -C 18 alkanesulfonates, C 8 -C 18 α-olefin sulfonates, sulfonated C 8 -C 18 fatty acids, C 1 -C 4 -Alkyl esters, C 6 -C 18 -alkylbenzenesulfonates, sulfonic succinic acid mono- and -di-C 1 -C 12 -alkyl esters, C 8 -C 18 -alkyl polyglycol ether carboxylates, C 8 -C 18 -N-acyltaurides, C 8 -C 18 -N Sarcosinates or C 8 -C 18 alkyl isethionates, which can also be present in an amount of 0.1 to 50% by weight, based on the total agent. It applies to all anionic surfactants that they are generally in the form of their ammonium, alkanolammonium, alkali or magnesium salts.
Auch weitere nichtionische Tenside können in einer Menge von 0,1 bis 40 Gew.-%, bezogen auf das gesamte Mittel, enthalten sein. Als nichtionische Tenside eignen sich z. B. Alkyl- oder Alkenyloligoglycoside der Formel R5O-[Z]x, in der R5 für einen Alkyl- oder Alkenylrest mit 8 - 22 C-Atomen, Z für einen Zuckerrest mit 5 oder 6 C-Atomen, insbesondere einen Glucoserest, und x für Zahlen von 1 - 10 steht, C8-C18-Fettsäuremono- und -diC1-C4-Alkanolamide, C8-C18-Fettsäureglucamide, Anlagerungsprodukte von Ethylenoxid und/oder Propylenoxid an C8-C18-Fettalkohole und an Mono- und Di-C8-C18-Fettsäureglyceride. Other nonionic surfactants can also be present in an amount of 0.1 to 40% by weight, based on the total agent. Suitable nonionic surfactants are, for. B. alkyl or alkenyl oligoglycosides of the formula R 5 O- [Z] x , in which R5 is an alkyl or alkenyl radical having 8-22 carbon atoms, Z is a sugar radical having 5 or 6 carbon atoms, in particular a glucose radical, and x represents numbers from 1 to 10, C 8 -C 18 fatty acid mono- and diC 1 -C 4 alkanolamides, C 8 -C 18 fatty acid glucamides, adducts of ethylene oxide and / or propylene oxide with C 8 -C 18 - Fatty alcohols and on mono- and di-C 8 -C 18 fatty acid glycerides.
In weiteren Ausführungsformen können die erfindungsgemäßen Reinigungsmittel zusätzliche oberflächenaktive Substanzen, z. B. Betaintenside oder Fettaminoxide enthalten. Fakultativ können weiterhin die in flüssigen Reinigungsmitteln für harte Oberflächen, z.B. Allzweckreinigern und manuellen Geschirrspülmitteln, enthaltenen üblichen Hilfsstoffe enthalten sein; bei diesen Stoffen handelt es sich um Builder, z. B. Glutarsäure, Bernsteinsäure, Adipinsäure, Weinsäure, Benzolhexacarbonsäure, Gluconsäure, Trinatriumcitrat; Lösungsmittel, wie z.B. Ethanol; Hydrotrope, z. B. Cumolsulfonat, Octylsulfat, Butylglucosid, Butylenglykol; Reinigungsverstärker; Viskositätsregler, z.B. synthetische Polymere wie Polyacrylate; pH-Regulatoren, z.B. Citronensäure, Triethanolamin oder NaOH; Konservierungsmittel, z.B. Glutaraldehyd; Färb- und Duftstoffe sowie Trübungsmittel oder auch Hautschutzmittel wie sie in EP-A-522 756 beschrieben sind. Die folgenden Beispiele sollen den Gegenstand näher erläutern, ohne ihn jedoch hierauf zu beschränken. In further embodiments, the cleaning agents according to the invention can contain additional surface-active substances, e.g. B. betaine surfactants or fatty amine oxides. The customary auxiliaries contained in liquid cleaning agents for hard surfaces, for example all-purpose cleaners and manual dishwashing agents, may also optionally be included; these substances are builders, e.g. B. glutaric acid, succinic acid, adipic acid, tartaric acid, benzene hexacarboxylic acid, gluconic acid, trisodium citrate; Solvents such as ethanol; Hydrotropes, e.g. B. cumene sulfonate, octyl sulfate, butyl glucoside, butylene glycol; Cleaning booster; Viscosity regulators, for example synthetic polymers such as polyacrylates; pH regulators, for example citric acid, triethanolamine or NaOH; Preservatives, eg glutaraldehyde; Dyes and fragrances as well as opacifiers or skin protection agents as described in EP-A-522 756. The following examples are intended to explain the subject in more detail, but without restricting it thereto.
Der pH-Wert der Reinigungsmittelformulierungen kann über einen weiteren Bereich variiert werden, da die Gluconsäureamide über einen weiteren Bereich hydrolysestabil sind, bevorzugt ist jedoch ein pH-Bereich von 5,5 bis 9,5. The pH of the detergent formulations can be varied over a wide range, since the gluconic amides are hydrolysis-stable over a wide range, but a pH range from 5.5 to 9.5 is preferred.
B e i s p i e l e Herstellung der Gluconsäureamide gemäß US 2,752,334 Example of the production of the gluconic amides according to US 2,752,334
Anwendungsbeispiele; Application examples;
Alle Formulierungen können neben den aufgeführten Bestandteilen die in Allzweckreinigern üblicherweise eingesetzten Komponenten wie Builder, Parfüm, Farbstoffe oder Verdickungsmittel bzw. die in manuellen Geschirrspülmitteln üblicherweise eingesetzten Komponenten wie Parfümstoffe, Farbstoffe, Trübungsmittel, Verdickungsmittel oder Hautschutzkomponenten enthalten. Der pH-Wert der Formulierungen liegt im allgemeinen zwischen 5,5 und 9,5, pH-Werte außerhalb dieses Bereiches sind jedoch ebenfalls möglich. In addition to the ingredients listed, all formulations can contain the components typically used in general-purpose cleaners, such as builders, perfume, dyes or thickeners, or the components typically used in manual dishwashing detergents, such as perfumes, dyes, opacifiers, thickeners or skin protection components. The pH of the formulations is generally between 5.5 and 9.5, but pH values outside this range are also possible.
In den Beispielen bedeuten: In the examples:
NRE: Narrow ränge ethoxylate (Ethoxylat mit eingeengter NRE: Narrow ranks ethoxylate (ethoxylate with restricted
Homologenverteilung)  Homolog distribution)
Hostapur SAS 60: C13-C18-sec-Alkansulfonsäure, Na-Salz der Fa. Hoechst PEG 400: Polyethylenglykol, MG = 400.000 Hostapur SAS 60: C 13 -C 18 -sec-alkanesulfonic acid, Na salt from Hoechst PEG 400: polyethylene glycol, MW = 400,000
PEG 200: Polyethylenglykol, MG = 200.000 PEG 200: polyethylene glycol, MW = 200,000
E0: Ethylenoxid E0: ethylene oxide
P0: Propylenoxid  P0: propylene oxide
APG 225: C8/10-Alkylpolyglucosid mit einem DP von 1,6 APG 225: C 8/10 alkyl polyglucoside with a DP of 1.6
DP: mittlerer Oligomerisierungsgrad bei Alkylpoly- bzw. DP: average degree of oligomerization with alkyl poly or
oligoglycosiden oligoglycosides
Verwendung der erfindungsgemäßen Reinigungsmittel als Handgeschirrspülmittel Use of the cleaning agents according to the invention as hand dishwashing agents
Beispiel 1: Example 1:
20 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz 20% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
10 % C12/14-Fettalkoholsulfat-Na-Salz 10% C 12/14 fatty alcohol sulfate Na salt
4 % Gluconsäure-C12/14-amid 4% gluconic acid C 12/14 amide
2 % Kokosfettsäureamidopropylbetain  2% coconut fatty acid amidopropyl betaine
9 % Ethanol  9% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 2: Example 2:
20 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz 20% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
10 % C12/14-Fettalkoholsulfat-Na-Salz 10% C 12/14 fatty alcohol sulfate Na salt
5 % Gluconsäure-C12/14-amid 5% gluconic acid C 12/14 amide
2 % Lauryldimethylaminoxid  2% lauryldimethylamine oxide
7 % Ethanol  7% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 3: Example 3:
18 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz 18% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
8 % C12/14-Fettsäuremethylestersulfonat-Na-Salz 8% C 12/14 fatty acid methyl ester sulfonate Na salt
8 % Gluconsäurekokosamid  8% gluconic acid cocamide
2 % Lauryldimethylaminoxid  2% lauryldimethylamine oxide
7 % Ethanol  7% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 4: Example 4:
20 % C12-Alkylbenzolsulfonat-Mg-Salz 20% C 12 alkyl benzene sulfonate Mg salt
8 % C12/14-Fettalkoholsulfat-Mg-Salz 8% C 12/14 fatty alcohol sulfate Mg salt
6 % Gluconsäure-C12/16-2E0-amid 2 % Lauryldimethylaminoxid 6% gluconic acid C 12/16 -2E0 amide 2% lauryldimethylamine oxide
5 % Ethanol  5% ethanol
3 % Cumolsulfonat  3% cumene sulfonate
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 5: Example 5:
12 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz12% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
4 % C12/14-Fettalkoholsulfat-Na-Salz 4% C 12/14 fatty alcohol sulfate Na salt
2 % Gluconsäure-C12-amid 2% gluconic acid C 12 amide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.42% C 12/14 alkyl polyglucoside with a DP of 1.4
3 % Ethanol 3% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 6: Example 6:
12 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz12% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
3 % Gluconsäure-C8/10-amid 3% gluconic acid C 8/10 amide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.42% C 12/14 alkyl polyglucoside with a DP of 1.4
4 % Ethanol 4% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 7: Example 7:
13 % C12/14-Fettalkoholsulfat-Na-Salz 13% C 12/14 fatty alcohol sulfate Na salt
3 % Gluconsäurekokos-3E0-amid  3% gluconic coconut 3E0 amide
3 % C12/14-Alkylpolyglucosid mit einem DP von 1.4 3 % Ethanol 3% C 12/14 alkyl polyglucoside with a DP of 1.4 3% ethanol
3 % PEG 400  3% PEG 400
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 8: Example 8:
12 % C12/18-Fettalkohol-(3E0)-ether-sulfat-Na-Salz12% C 12/18 fatty alcohol (3E0) ether sulfate Na salt
4 % C12/18-Fettalkoholsulfat 4% C 12/18 fatty alcohol sulfate
2 % Gluconsäure-C12/14-amid 2 % Kokosfettsäuremonoalkanolamid 2% gluconic acid C 12/14 amide 2% coconut fatty acid monoalkanolamide
2 % 1,2-Propylenglykol  2% 1,2-propylene glycol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 9: Example 9:
15 % C12-Alkylbenzolsulfonat-Mg-Salz 15% C 12 alkyl benzene sulfonate Mg salt
5 % C12/14-Fettalkoholsulfat 5% C 12/14 fatty alcohol sulfate
3 % Gluconsäure-C12/14_fettsäureamid 3% gluconic acid C 12/14 fatty acid amide
5 % Na-Sulfobernsteinsäurediisooctylester  5% diisooctyl Na sulfosuccinate
3 % Ethanol  3% ethanol
2 % PEG 600  2% PEG 600
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 10: Example 10:
15 % C12/14-Fettalkoholether(3E0)sulfat-Mg-Salz 15% C 12/14 fatty alcohol ether (3E0) sulfate Mg salt
1,5 % Gluconsäure-C12/14-amid 1.5% gluconic acid C 12/14 amide
2 % Kokosfettsäureamidopropylbetain  2% coconut fatty acid amidopropyl betaine
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 11; Example 11;
15 % C12/14-Fettalkoholether(3E0)sulfat-Mg-Salz 15% C 12/14 fatty alcohol ether (3E0) sulfate Mg salt
1,5 % Gluconsäure-N-C12/14-N-methylamid 1.5% gluconic acid-NC 12/14 -N-methylamide
1,5 % Laurylfettsäure-N-methylglucamid  1.5% lauryl fatty acid N-methylglucamide
2 % Ethanol  2% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 12: Example 12:
15 % C12/14-Fettalkoholether-(3E0)-sulfat-Na-Salz (NRE-Ethoxylat)15% C 12/14 fatty alcohol ether (3E0) sulfate Na salt (NRE ethoxylate)
4 % C12/14-Fettalkoholsulfat-Na-Salz 4% C 12/14 fatty alcohol sulfate Na salt
3 % Gluconsäuredecylamid  3% gluconic acid decylamide
4 % Ethanol  4% ethanol
Rest auf 100 % Wasser Bei spiel 13: Rest on 100% water Example 13:
12 % C12/14-Fettalkoholether-(2-5E0)-sulfat-Na-Salz (NRE-Ethoxylat) 4 % C12/14-Fettalkoholsulfat-Na-Salz 12% C 12/14 fatty alcohol ether (2-5E0) sulfate Na salt (NRE ethoxylate) 4% C 12/14 fatty alcohol sulfate Na salt
3 % Gluconsäurelaurylamid  3% gluconic acid laurylamide
3 % C12/14-Alkylpolyxylosid mit einem DP von 1.4 3% C 12/14 alkyl polyxyloside with a DP of 1.4
4 % Ethanol  4% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 14: Example 14:
10 % C12/14-Fettalkoholether-(3E0)-sulfat-Na-Salz 10% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
4 % C12/14-Fettalkoholsulfat-Na-Salz 4% C 12/14 fatty alcohol sulfate Na salt
2 % Gluconsäurekokosamid  2% gluconic cocosamide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 2% C 12/14 alkyl polyglucoside with a DP of 1.5
2 % Kokosfettsäuretaurid-Na-Salz  2% coconut fatty acid, sodium salt
4 % Ethanol  4% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 15: Example 15:
12 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz 12% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
4 % C12/14-Fettalkoholsulfat-Na-Salz 4% C 12/14 fatty alcohol sulfate Na salt
2 % Gluconsäure-C8/18-3E0-amid 2% gluconic acid C 8/18 -3E0 amide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 2% C 12/14 alkyl polyglucoside with a DP of 1.5
2 % Kokosfettsäureamidopropylbetain  2% coconut fatty acid amidopropyl betaine
4 % Ethanol  4% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 16: Example 16:
12 % C12/14-Fettalkoholether(3E0)sulfat-Na-Salz 12% C 12/14 fatty alcohol ether (3E0) sulfate Na salt
6 % Kokosfettsäuremonoglycerid + 10 E0  6% coconut fatty acid monoglyceride + 10 E0
2 % Gluconsäure-C12-amid 2% gluconic acid C 12 amide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 2% C 12/14 alkyl polyglucoside with a DP of 1.5
4 % Ethanol Rest auf 100 % Wasser Beispiel 17: 4% ethanol Remainder on 100% water Example 17:
12 % C12/14-Oxoalkoholether-(2E0)-sulfat-Na-Salz 12% C 12/14 oxo alcohol ether (2E0) sulfate Na salt
6 % Kokosfettsäuremonoglycerid + 10 E0  6% coconut fatty acid monoglyceride + 10 E0
2 % Gluconsäurekokosamid  2% gluconic cocosamide
2 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 2% C 12/14 alkyl polyglucoside with a DP of 1.5
4 % Ethanol  4% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 18: Example 18:
14 % C12/14-Fettalkoholether(2,5E0)sulfat-Na-Salz (NRE) 6 % C10/14-Fettalkohol + 8 E0 14% C 12/14 fatty alcohol ether (2.5E0) sulfate Na salt (NRE) 6% C 10/14 fatty alcohol + 8 E0
2 % Gluconsäure-C12/14-amid 2% gluconic acid C 12/14 amide
3 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 1,5 % Amidoethyl-N-2-hydroxyethylglycinat 3% C 12/14 alkyl polyglucoside with a DP of 1.5 1.5% amidoethyl-N-2-hydroxyethylglycinate
6 % Ethanol  6% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 19: Example 19:
14 % C12/14-Fettalkoholether-(1,2E0)-sulfat-Na-Salz (NRE) 6 % C10/14-Fettalkohol + 1,2 PO + 8 E0 14% C 12/14 fatty alcohol ether (1,2E0) sulfate Na salt (NRE) 6% C 10/14 fatty alcohol + 1,2 PO + 8 E0
2 % Gluconsäure-C10/12-amid 2% gluconic acid C 10/12 amide
3 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 1,5 % Amidoethyl-N-2-hydroxyethylglycinat 3% C 12/14 alkyl polyglucoside with a DP of 1.5 1.5% amidoethyl-N-2-hydroxyethylglycinate
6 % Ethanol  6% ethanol
Rest auf 100 % Wasser  Rest on 100% water
Beispiel 20: Example 20:
29 % C12/14-Fettalkoholether-(1,2E0)-sulfat-Mg-Salz (NRE) 10 % C12/14-Fettalkoholsulfat-Mg-Salz 29% C 12/14 fatty alcohol ether (1,2E0) sulfate Mg salt (NRE) 10% C 12/14 fatty alcohol sulfate Mg salt
10 % C10/14-Fettalkohol + 1,2 PO + 8 E0 8 % Gluconsäure-C16/18-3E0-amid 10% C 10/14 fatty alcohol + 1.2 PO + 8 E0 8% gluconic acid C 16/18 -3E0 amide
3 % C12/14-Alkylpolyglucosid mit einem DP von 1.5 12 % C4-Alkylpolyglucosid mit einem DP von 1.5 8 % PEG 200 3% C 12/14 alkyl polyglucoside with a DP of 1.5 12% C 4 alkyl polyglucoside with a DP of 1.5 8% PEG 200
10 % Ethanol 10% ethanol
Rest auf 100 % Wasser Rest on 100% water
Verwendung der erfindungsgemäßen Reinigungsmittel als Allzweck- und Haushaltsreiniger: Use of the cleaning agents according to the invention as general-purpose and household cleaners:
Beispiel 21: Example 21:
45,0 Gew.-% APG 225 45.0 wt% APG 225
13,0 Gew.-% C12-Fettsäuremethylester + 13 EO 13.0% by weight of C 12 fatty acid methyl ester + 13 EO
3,0 Gew.-% Gluconsäure-C6/10-amid 3.0% by weight of gluconic acid C 6/10 amide
5,0 Gew.-% Palmkernfettsäure  5.0% by weight of palm kernel fatty acid
1,0 Gew.-% Zitronensäure  1.0% by weight of citric acid
10,0 Gew.-% Cumolsulfonat  10.0% by weight cumene sulfonate
X Gew.-% Kalilauge zur Einstellung des pH-Wertes des Fertigproduktes auf pH 8  X% by weight of potassium hydroxide solution for adjusting the pH of the finished product to pH 8
ad 100,0 Gew.-% Wasser, Färb- und Duftstoffe ad 100.0% by weight of water, dyes and fragrances
Beispiel 22: Example 22:
2,0 Gew.-% APG 225 2.0% by weight APG 225
0,5 Gew.-% Butylpolyglucosid  0.5% by weight of butyl polyglucoside
0,5 Gew.-% Gluconsäure-C8/10-amid + 1,7 E0 0.5% by weight of gluconic acid C 8/10 amide + 1.7 E0
1,0 Gew.-% Palmkernfettsäure  1.0% by weight of palm kernel fatty acid
2,0 Gew.-% Dicarbonsäuregemisch (Glutar-, Adipin- und Bernstein  2.0% by weight of dicarboxylic acid mixture (glutaric, adipic and amber
säure)  acid)
0,05 Gew.-% Polyethylenoxid, MG 600000  0.05% by weight polyethylene oxide, MW 600000
2,0 Gew.-% Butylglykol  2.0% by weight of butyl glycol
X Gew.-% Natronlauge zur Einstellung auf pH 8  X% by weight sodium hydroxide solution to adjust to pH 8
ad 100,0 Gew.-% Wasser, Färb- und Duftstoffe, Konservierungsmittel ad 100.0% by weight of water, dyes and fragrances, preservatives
Beispiel 23: Example 23:
0,6 Gew.-% C10-Alkylpolyglucosid 0.6% by weight of C 10 alkyl polyglucoside
0,05 Gew.-% Gluconsäure-C8/10-1,7E0-amid 0.05 wt% gluconic acid C 8/10 -1.7E0 amide
0,001 Gew.-% Kokosfettsäure  0.001% by weight coconut fatty acid
9,0 Gew.-% Ethanol X Gew.-% Ammoniak zur Einstellung auf pH 8,5 ad 100,0 Gew.-% Wasser 9.0% by weight of ethanol X wt .-% ammonia to adjust to pH 8.5 ad 100.0 wt .-% water
Beispiel 24: Example 24:
12 Gew.-% C10-Alkylpolyglucosid 12% by weight of C 10 alkyl polyglucoside
6 Gew.-% C8/10-Fettalkohol + 4 EO 6% by weight of C 8/10 fatty alcohol + 4 EO
1 Gew.-% Gluconsäure-C12/14+6E0-amid 1% by weight gluconic acid C 12/14 + 6E0 amide
2 Gew.-% C12/14-Fettalkoholsulfat 2% by weight of C 12/14 fatty alcohol sulfate
5 Gew.-% Ethanol  5% by weight ethanol
X Gew.-% Natronlauge zur Einstellung auf pH 7-7,5 ad 100,0 Gew.-% Wasser  X% by weight sodium hydroxide solution to adjust to pH 7-7.5 ad 100.0% by weight water
Beispiel 25: Example 25:
12 Gew.-% C10-Alkylpolyxylosid 12% by weight of C 10 alkyl polyxyloside
8 Gew.-% C12-Fettalkohol + 6 E0 8% by weight of C 12 fatty alcohol + 6 E0
1 Gew.-% Gluconsäure-C12/14+6E0-amid 1% by weight gluconic acid C 12/14 + 6E0 amide
5 Gew.-% Ethanol  5% by weight ethanol
X Gew.-% Kalilauge zur Einstellung auf pH 7-7,5 ad 100,0 Gew.-% Wasser  X% by weight potassium hydroxide solution to adjust to pH 7-7.5 ad 100.0% by weight water
Beispiel 26: Example 26:
10 Gew.-% C8/10-Alkylpolyglucosid 10% by weight of C 8/10 alkyl polyglucoside
6 Gew.-% C12-Fettsäuremethylester + 15 E06% by weight of C 12 fatty acid methyl ester + 15 E0
2 Gew.-% Gluconsäure-C8/10+2E0-amid 2% by weight of gluconic acid C 8/10 + 2E0 amide
2 Gew.-% Hostapur SAS 60  2% by weight of Hostapur SAS 60
3 Gew.-% Cumolsulfonat  3% by weight cumene sulfonate
1,5 Gew.-% Kokosfettsäure  1.5% by weight coconut fatty acid
5 Gew.-% Ethanol  5% by weight ethanol
X Gew.-% NaOH zur Einstellung auf pH 7-7,5 ad 100,0 Gew.-% Wasser  X% by weight NaOH to adjust to pH 7-7.5 ad 100.0% by weight water

Claims

P a t e n t a n s p r ü c h e Patent claims
1. Verwendung von Gluconsäureamiden der Formel I 1. Use of gluconic amides of the formula I
Figure imgf000016_0001
in der R1 und R2 unabhängig voneinander Wasserstoffe oder Methylgruppen bedeuten, n und m unabhängig voneinander Null oder ganze Zahlen von 1 bis 18 darstellen, R3 Wasserstoff, eine Methyl- oder eine Ethylgruppe darstellt und R4 für eine lineare oder verzweigte, gesättigte oder ungesättigte C6-C22-Alkylgruppe steht, als oberflächenaktive Substanzen in Spül- und Reinigungsmitteln zum Spülen und Reinigen harter Oberflächen.
Figure imgf000016_0001
in which R 1 and R 2 independently represent hydrogen or methyl groups, n and m independently represent zero or integers from 1 to 18, R 3 represents hydrogen, a methyl or an ethyl group and R 4 represents a linear or branched, saturated or unsaturated C 6 -C 22 alkyl group, as surface-active substances in detergents and cleaning agents for rinsing and cleaning hard surfaces.
2. Verwendung nach Anspruch 1, dadurch gekennzeichnet, daß in der Formel I n und m gleich Null sind, R3 für Wasserstoff und R4 für eine lineare oder verzweigte gesättigte oder ungesättigte C12-C18-Alkylgruppe steht. 2. Use according to claim 1, characterized in that in formula I n and m are zero, R 3 is hydrogen and R 4 is a linear or branched saturated or unsaturated C 12 -C 18 alkyl group.
PCT/EP1995/000568 1994-02-25 1995-02-16 Use of glyconic-acid amides as surfactants for cleaning and rinsing hard surfaces WO1995023203A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000065005A2 (en) * 1999-04-22 2000-11-02 Cognis Deutschland Gmbh Cleaning agents for hard surfaces

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007008868A1 (en) 2007-02-21 2008-08-28 Henkel Ag & Co. Kgaa Automatic dishwasher detergent containing a sugar acid amide, e.g. N-octyl-D-gluconamide, useful especially for removing tenacious and-or burnt-on dirt from hard surfaces or textiles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2523962A1 (en) * 1982-03-24 1983-09-30 Centre Nat Rech Scient Detergent aldonic acid amide(s) - are prepd. from acid and long chain amine
EP0550278A1 (en) * 1991-12-31 1993-07-07 Unilever Plc Detergent compositions comprising nonionic glycolipid surfactants
JPH05221946A (en) * 1992-02-13 1993-08-31 Toho Chem Ind Co Ltd New nonionic surfactant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2523962A1 (en) * 1982-03-24 1983-09-30 Centre Nat Rech Scient Detergent aldonic acid amide(s) - are prepd. from acid and long chain amine
EP0550278A1 (en) * 1991-12-31 1993-07-07 Unilever Plc Detergent compositions comprising nonionic glycolipid surfactants
JPH05221946A (en) * 1992-02-13 1993-08-31 Toho Chem Ind Co Ltd New nonionic surfactant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000065005A2 (en) * 1999-04-22 2000-11-02 Cognis Deutschland Gmbh Cleaning agents for hard surfaces
WO2000065005A3 (en) * 1999-04-22 2001-04-05 Cognis Deutschland Gmbh Cleaning agents for hard surfaces

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