EP0785922A1 - Sulphonated mixed ethers as wetting agents and starting materials for detergents - Google Patents

Sulphonated mixed ethers as wetting agents and starting materials for detergents

Info

Publication number
EP0785922A1
EP0785922A1 EP96925688A EP96925688A EP0785922A1 EP 0785922 A1 EP0785922 A1 EP 0785922A1 EP 96925688 A EP96925688 A EP 96925688A EP 96925688 A EP96925688 A EP 96925688A EP 0785922 A1 EP0785922 A1 EP 0785922A1
Authority
EP
European Patent Office
Prior art keywords
wetting agents
alkyl radical
detergents
salts
mixtures
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Withdrawn
Application number
EP96925688A
Other languages
German (de)
French (fr)
Inventor
Klaus Kwetkat
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huels AG
Original Assignee
Huels AG
Chemische Werke Huels AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19615272A external-priority patent/DE19615272A1/en
Application filed by Huels AG, Chemische Werke Huels AG filed Critical Huels AG
Publication of EP0785922A1 publication Critical patent/EP0785922A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/04—Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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

Definitions

  • the invention relates to sulfonated alkyl polyalkylene glycol ethers and their mixtures, processes for the preparation of these compounds or their mixtures and their use as wetting agents and detergent raw materials.
  • Hydroxy mixed ethers (I) and sulfated hydroxy mixed ethers (II) have been known for some time and are described in DE-OSS 33 45 349 and 37 23 354:
  • R straight chain alkyl group having 6 to 16 carbon atoms
  • R straight-chain or branched alkyl radical with 4 to 16 carbon atoms
  • R 3 H or an alkyl radical having 1 to 8 carbon atoms
  • R 4 H or a methyl radical n a number from 7 to 12
  • foam-suppressing additives or wetting agents and detergent raw materials.
  • This object is achieved by the present invention in which sultones from olefins, preferably ⁇ -olefins, are reacted with alcohols and / or alcohol alkoxylates and give the desired low-foaming wetting agents.
  • the invention therefore relates to sulfonic acids, their salts or their mixtures of the general formula (III)
  • R is hydrogen or a straight-chain or branched alkyl radical having 1 to 12 C atoms, R : a straight-chain or branched alkyl radical having 6 to 22 C atoms, R ; a straight-chain or branched alkyl radical having 4 to 16 carbon atoms, R 3 H or an alkyl radical having 1 to 3 carbon atoms, M hydrogen or an equivalent of an alkali metal, alkaline earth metal, ammonium or alkylammonium ion, n is a number from 1 to 3 and m are a number from 0 to 20
  • mixed alkoxide units can also occur and then the sequence of the alkoxide units is arbitrary, a process for the preparation of these sulfonic acids / salts and their use as low-foaming wetting agents and / or detergent raw materials.
  • the compounds according to the invention are further distinguished by the fact that they can be adapted very flexibly to the application requirements by selecting the starting compounds.
  • the wetting effect can be achieved by using slightly branched alcohols and / or alkoxylates, e.g. the alkoxylates of 2-ethylhexanol, increase; m has an influence on the foaming and wetting properties.
  • the sultones are produced using known processes. Instead of the hydrolysis customary in the production of ⁇ -olefin sulfonates, the reaction with alcohols and / or takes place in the process according to the invention
  • reaction mixture was then stirred at 40 ° C. with MARLIPAL 24/40 (C :: , --- alcohol with a degree of ethoxylation of 4.0) at a temperature of 150 ° C. until the sultones present in the reaction mixture were completely opened.
  • reaction mixture was then stored at 40 ° C with MARLIPAL 24/20 (C lc, 4 -A1kohol with a degree of ethoxylation of 2.0) and stirred at a temperature of 145 ° C up to the complete opening of the vorlie- in the reaction mixture constricting sultones.
  • MARLIPAL 24/20 C lc, 4 -A1kohol with a degree of ethoxylation of 2.0

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention relates to sulphonated alkyl polyalkylene glycol ethers and their mixtures of the formula (III), a process producing said compounds or their mixtures and their use as wetting agents and starting materials for detergents.

Description

SULFONIERTE MISCHETHER ALS NETZMITTEL UND WASCHMITTELROHSTOFF SULPHONED MIXING THERMAL AS WET AND DETERGENT RAW MATERIAL
Die Erfindung betrifft sulfonierte Alkylpolyalkylenglykolether und ihre Gemische, Verfahren zur Herstellung dieser Verbindungen bzw. ihrer Ge¬ mische und ihre Verwendung als Netzmittel und Waschmittelrohstoffe.The invention relates to sulfonated alkyl polyalkylene glycol ethers and their mixtures, processes for the preparation of these compounds or their mixtures and their use as wetting agents and detergent raw materials.
Hydroxymischether (I) und sulfatierte Hydroxymischether (II) sind bereits längere Zeit bekannt und werden in den DE-OSS 33 45 349 bzw. 37 23 354 be¬ schrieben:Hydroxy mixed ethers (I) and sulfated hydroxy mixed ethers (II) have been known for some time and are described in DE-OSS 33 45 349 and 37 23 354:
(I): X = H(I): X = H
(II) X = S0,Na(II) X = S0, Na
R:: geradkettiger Alkylrest mit 6 bis 16 C-Atomen R: straight chain alkyl group having 6 to 16 carbon atoms
R: geradkettiger oder verzweigter Alkylrest mit 4 bis 16 C-AtomenR : straight-chain or branched alkyl radical with 4 to 16 carbon atoms
R3 H oder ein Alkylrest mit 1 bis 8 C-AtomenR 3 H or an alkyl radical having 1 to 8 carbon atoms
R4 H oder ein Methylrest n: eine Zahl von 7 bis 12R 4 H or a methyl radical n: a number from 7 to 12
Sie werden als schaumdrückende Zusätze bzw. Netzmittel und Waschmittelroh¬ stoffe beschrieben.They are described as foam-suppressing additives or wetting agents and detergent raw materials.
Den bekannten Verbindungstypen ist der Nachteil gemeinsam, daß man Epoxide für ihre Herstellung benötigt, was dazu führt, daß als Produkte entweder multifunktionelle, stark verzweigte Verbindungen vorliegen, wenn man von epoxidierten Pflanzenölen ausgeht, oder daß sehr teure α-Epoxide eingesetzt werden müssen. In beiden Fällen führt der Einsatz der genannten Epoxide dazu, daß die Verbindungen kaum kommerziell hergestellt werden können.The known types of compounds have the disadvantage in common that epoxides are required for their preparation, which means that products are either multifunctional, highly branched compounds when starting from epoxidized vegetable oils, or that very expensive α-epoxides have to be used. In both cases, the use of the epoxides mentioned means that the compounds can hardly be produced commercially.
Da nach wie vor ein Bedarf an schaumarmen Netzmitteln, die zudem auch als Reinigungsmittel eingesetzt werden können, vorhanden ist, bestand die Auf- gäbe, strukturell ähnliche Verbindungen auf der Basis von preiswerten Roh¬ stoffen herzustellen.Since there is still a need for low-foaming wetting agents, which can also be used as cleaning agents, there was a there would be structurally similar connections on the basis of inexpensive raw materials.
Diese Aufgabe wird durch die vorliegende Erfindung gelöst, bei der Sultone aus Olefinen, bevorzugt α-Olefinen, mit Alkoholen und/oder Alkoholalkoxylaten umgesetzt werden und die gewünschten schaumarmen Netzmittel ergeben.This object is achieved by the present invention in which sultones from olefins, preferably α-olefins, are reacted with alcohols and / or alcohol alkoxylates and give the desired low-foaming wetting agents.
Gegenstand der Erfindung sind daher Sulfonsäuren, deren Salze oder deren Gemische der allgemeinen Formel (III)The invention therefore relates to sulfonic acids, their salts or their mixtures of the general formula (III)
R1 R3 i iR 1 R 3 ii
M03S - (CH2)„ CR OCH—CH2- OR2 (Bl)M0 3 S - (CH 2 ) "CR OCH — CH 2 - OR 2 (Bl)
in derin the
R Wasserstoff oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 12 C-Atomen, R: einen geradkettigen oder verzweigten Alkylrest mit 6 bis 22 C-Atomen, R; einen geradkettigen oder verzweigten Alkylrest mit 4 bis 16 C-Atomen, R3 H oder einen Alkylrest mit 1 bis 3 C-Atomen, M Wasserstoff oder ein Äquivalent eines Alkali-, Erdalkali-, Ammonium- oder Alkylammoniumions, n eine Zahl von 1 bis 3 und m eine Zahl von 0 bis 20R is hydrogen or a straight-chain or branched alkyl radical having 1 to 12 C atoms, R : a straight-chain or branched alkyl radical having 6 to 22 C atoms, R ; a straight-chain or branched alkyl radical having 4 to 16 carbon atoms, R 3 H or an alkyl radical having 1 to 3 carbon atoms, M hydrogen or an equivalent of an alkali metal, alkaline earth metal, ammonium or alkylammonium ion, n is a number from 1 to 3 and m are a number from 0 to 20
bedeutet, wobei auch gemischte Alkoxideinheiten auftreten können und dann die Reihenfolge der Alkoxideinheiten beliebig ist, ein Verfahren zur Herstellung dieser Sulfonsäuren/Salze und ihre Verwendung als schaumarme Netzmittel und/oder Waschmittelrohstoffe.means that mixed alkoxide units can also occur and then the sequence of the alkoxide units is arbitrary, a process for the preparation of these sulfonic acids / salts and their use as low-foaming wetting agents and / or detergent raw materials.
Mit dieser Vorgehensweise vermeidet man einerseits die teuren α-Epoxide und spart zudem einen Reaktionsschritt ein, da durch die Öffnung der Sultone eine Sulfonsäure entsteht, die nur noch neutralisiert werden muß. Ein Vorteil der erfindungsgemäßen Verbindungen gegenüber anderen Netzmitteln und Waschmittelrohstoffen nach dem Stand der Technik besteht darin, daß sie kaum zur Schaumbildung neigen und ein vergleichbares oder besseres Netz¬ verhalten zeigen.This procedure avoids on the one hand the expensive α-epoxides and also saves one reaction step, since the opening of the sultones creates a sulfonic acid that only needs to be neutralized. An advantage of the compounds according to the invention over other wetting agents and detergent raw materials according to the prior art is that they hardly have any tendency to foam and show comparable or better wetting behavior.
Die erfindungsgemäßen Verbindungen zeichnen sich weiterhin dadurch aus, daß sie über die Auswahl der Ausgangsverbindungen recht flexibel an die anwen¬ dungstechnischen Erfordernisse angepaßt werden können. So läßt sich die Netzwirkung durch den Einsatz leicht verzweigter Alkohole und/oder Alkoxy- late, wie z.B. den Alkoxylaten des 2-Ethylhexanols, erhöhen; m hat Einfluß auf das Schäum- und das Netzvermögen.The compounds according to the invention are further distinguished by the fact that they can be adapted very flexibly to the application requirements by selecting the starting compounds. For example, the wetting effect can be achieved by using slightly branched alcohols and / or alkoxylates, e.g. the alkoxylates of 2-ethylhexanol, increase; m has an influence on the foaming and wetting properties.
Die Herstellung der Sultone erfolgt nach bekannten Verfahren. Statt der bei der Herstellung von α-Olefinsulfonaten üblichen Hydrolyse erfolgt bei dem erfindungsgemäßen Verfahren die Umsetzung mit Alkoholen und/oderThe sultones are produced using known processes. Instead of the hydrolysis customary in the production of α-olefin sulfonates, the reaction with alcohols and / or takes place in the process according to the invention
Alkoholalkoxylaten bei Temperaturen von 40 bis 160 °C, die darauffolgende Neutralisierung erfolgt bei 30 bis 90 °C entweder mit wäßrigen Basen oder mit Trialkyl- bzw. Trialkanolaminen.Alcohol alkoxylates at temperatures of 40 to 160 ° C, the subsequent neutralization is carried out at 30 to 90 ° C either with aqueous bases or with trialkyl or trialkanolamines.
Die folgenden Beispiele sollen den Erfindungsgegenstand verdeutlichen, ohne ihn darauf einzuschränken.The following examples are intended to illustrate the subject matter of the invention without restricting it.
Beispiel 1:Example 1:
1,19 mol 1-Dodecen wurden bei einer Temperatur von 30 °C in einem geeigneten Reaktor mit einem S03/Luft-Gemisch (4 Vol.-% S03) , S03 : Olefin entsprach ei¬ nem Verhältnis von 1,06 zu 1,0, umgesetzt und das Reaktionsgemisch bei 35 °C für 10 Minuten gealtert.1.19 mol of 1-dodecene were at a temperature of 30 ° C in a suitable reactor with a S0 3 / air mixture (4 vol.% S0 3 ), S0 3 : olefin corresponded to a ratio of 1.06 to 1.0, reacted and the reaction mixture aged at 35 ° C for 10 minutes.
Das Reaktionsgemisch wurde anschließend bei 40 °C mit MARLIPAL 24/40 (C::,---Alkohol mit einem Ethoxylierungsgrad von 4,0) bei einer Temperatur von 150 °C bis zu vollständigen Öffnung der im Reaktionsgemisch vorliegenden Sultone gerührt.The reaction mixture was then stirred at 40 ° C. with MARLIPAL 24/40 (C :: , --- alcohol with a degree of ethoxylation of 4.0) at a temperature of 150 ° C. until the sultones present in the reaction mixture were completely opened.
Das Reaktionsprodukt wurde mit 40 %iger wäßriger Natronlauge bei 60 °C neu- tralisiert. Das :3C NMR Spektrum zeigte ein Gemisch von 65 mol-% des ge¬ wünschten Produktes neben Alkensulfonat. Die anwendungstechnische Charakterisierung, Draves-Test und Schlagschaum nach DIN 53902, Teil 1, er¬ gab sehr gute Werte. Beispiel 2:The reaction product was neutralized with 40% aqueous sodium hydroxide solution at 60 ° C. The : 3 C NMR spectrum showed a mixture of 65 mol% of the desired product in addition to alkene sulfonate. The application-technical characterization, Draves test and blow foam according to DIN 53902, part 1, gave very good values. Example 2:
1,0 mol 1-Decen wurden bei einer Temperatur von 30 °C in einem geeigneten Reaktor mit einem S03/Luft-Gemisch (4 Vol.-% S03) , S03 : Olefin entsprach einem Verhältnis von 1,05 zu 1,0, umgesetzt und das Reaktionsgemisch bei 33 °C für 10 Minuten gealtert.1.0 mol of 1-decene were at a temperature of 30 ° C in a suitable reactor with a S0 3 / air mixture (4 vol .-% S0 3 ), S0 3 : olefin corresponded to a ratio of 1.05 to 1 , 0, implemented and the reaction mixture aged at 33 ° C for 10 minutes.
Das Reaktionsgemisch wurde anschließend bei 40 °C mit MARLIPAL 24/20 (Clc,:4-A1kohol mit einem Ethoxylierungsgrad von 2,0) bei einer Temperatur von 145 °C bis zur vollständigen Öffnung der im Reaktionsgemisch vorlie- genden Sultone gerührt.The reaction mixture was then stored at 40 ° C with MARLIPAL 24/20 (C lc, 4 -A1kohol with a degree of ethoxylation of 2.0) and stirred at a temperature of 145 ° C up to the complete opening of the vorlie- in the reaction mixture constricting sultones.
Das Reaktionsprodukt wurde mit 40 %iger wäßriger Natronlauge bei 60 °C neu¬ tralisiert. Das 13C NMR Spektrum zeigte ein Gemisch von 60 Mol-% des ge¬ wünschten Produktes neben Alkensulfonat. Die anwendungstechnische Charakterisierung, Draves-Test und Schlagschaum nach DIN 53902, Teil 1, er¬ gab dem Beispiel 1 vergleichbare, gute Werte. The reaction product was neutralized with 40% aqueous sodium hydroxide solution at 60 ° C. The 13 C NMR spectrum showed a mixture of 60 mol% of the desired product in addition to alkene sulfonate. The application-technical characterization, Draves test and whipped foam according to DIN 53902, Part 1, gave Example 1 comparable, good values.

Claims

Patentansprüche;Claims;
1. Sulfonsäuren, deren Salze oder deren Gemische der allgemeinen Formel (III)1. sulfonic acids, their salts or their mixtures of the general formula (III)
R1 R3 ι M03S - (CH2)n CR OCH-CH2- OR2 (■)R 1 R 3 ι M0 3 S - (CH 2 ) n CR OCH-CH 2 - OR 2 (■)
in derin the
R Wasserstoff oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 12 C-Atomen,R is hydrogen or a straight-chain or branched alkyl radical having 1 to 12 carbon atoms,
R: einen geradkettigen oder verzweigten Alkylrest mit 6 bis 22 C-Atomen,R : a straight-chain or branched alkyl radical having 6 to 22 carbon atoms,
R: einen geradkettigen oder verzweigten Alkylrest mit 4 bis 16 C-Atomen,R : a straight-chain or branched alkyl radical having 4 to 16 carbon atoms,
R3 H oder einen Alkylrest mit 1 bis 3 C-Atomen,R 3 is H or an alkyl radical having 1 to 3 C atoms,
M Wasserstoff oder ein Äquivalent eines Alkali-, Erdalkali-, Ammonium- oder Alkylammoniumions, n eine Zahl von 1 bis 3 und m eine Zahl von 0 bis 20M is hydrogen or an equivalent of an alkali, alkaline earth, ammonium or alkylammonium ion, n is a number from 1 to 3 and m is a number from 0 to 20
bedeutet, wobei auch gemischte Alkoxideinheiten auftreten können und dann die Reihenfolge der Alkoxideinheiten beliebig ist.means, mixed alkoxide units can also occur and the sequence of the alkoxide units is then arbitrary.
Verfahren zur Herstellung von Sulfonsäuren, deren Salzen oder deren Ge¬ mischen nach Anspruch 1, dadurch gekennzeichnet, daß Sultone mit Alkoholen und/oder Alkoholalkoxylaten bei Temperaturen von 40 bis 160 °C umgesetzt und bei 30 bis 90 °C mit wäßrigen Basen, Trialkyl- oder Trialkanolaminen umgesetzt werden.A process for the preparation of sulfonic acids, their salts or their mixtures according to claim 1, characterized in that sultones are reacted with alcohols and / or alcohol alkoxylates at temperatures from 40 to 160 ° C and at 30 to 90 ° C with aqueous bases, trialkyl or trialkanolamines are implemented.
3. Verwendung von Sulfonsäuren, deren Salzen oder deren Gemischen nach An- spruch 1 als Netzmittel.3. Use of sulfonic acids, their salts or their mixtures as claimed in claim 1 as wetting agents.
4. Verwendung von Sulfonsäuren, deren Salzen oder deren Gemischen nach An¬ spruch 1 als Waschmittelrohstoff. 4. Use of sulfonic acids, their salts or their mixtures according to claim 1 as raw material for detergents.
EP96925688A 1995-08-12 1996-07-09 Sulphonated mixed ethers as wetting agents and starting materials for detergents Withdrawn EP0785922A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19529768 1995-08-12
DE19529768 1995-08-12
DE19615272 1996-04-18
DE19615272A DE19615272A1 (en) 1995-08-12 1996-04-18 Sulphonated mixed ethers, processes for their preparation and their use
PCT/EP1996/002993 WO1997007095A1 (en) 1995-08-12 1996-07-09 Sulphonated mixed ethers as wetting agents and starting materials for detergents

Publications (1)

Publication Number Publication Date
EP0785922A1 true EP0785922A1 (en) 1997-07-30

Family

ID=26017655

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96925688A Withdrawn EP0785922A1 (en) 1995-08-12 1996-07-09 Sulphonated mixed ethers as wetting agents and starting materials for detergents

Country Status (3)

Country Link
EP (1) EP0785922A1 (en)
AU (1) AU6612996A (en)
WO (1) WO1997007095A1 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE610499A (en) * 1960-11-22
GB1344987A (en) * 1970-06-04 1974-01-23 Agfa Gevaert Film-fomring hydrophilic compositions and photographic elements containing a layer thereof
DE3723354A1 (en) * 1987-07-15 1989-01-26 Henkel Kgaa SULFATED HYDROXY MIXERS, METHOD FOR THEIR PRODUCTION AND THEIR USE

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9707095A1 *

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WO1997007095A1 (en) 1997-02-27
AU6612996A (en) 1997-03-12

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