EP0485500A1 - Concentres de tensio-actifs anioniques aqueux avec des sulphonates d'acide oleique comme regulateurs de viscosite. - Google Patents

Concentres de tensio-actifs anioniques aqueux avec des sulphonates d'acide oleique comme regulateurs de viscosite.

Info

Publication number
EP0485500A1
EP0485500A1 EP90912661A EP90912661A EP0485500A1 EP 0485500 A1 EP0485500 A1 EP 0485500A1 EP 90912661 A EP90912661 A EP 90912661A EP 90912661 A EP90912661 A EP 90912661A EP 0485500 A1 EP0485500 A1 EP 0485500A1
Authority
EP
European Patent Office
Prior art keywords
oleic acid
alkyl
aqueous
sulfates
weight
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.)
Granted
Application number
EP90912661A
Other languages
German (de)
English (en)
Other versions
EP0485500B1 (fr
Inventor
Ansgar Behler
Brigitte Giesen
Hermann Anzinger
Karl-Heinz Linde
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0485500A1 publication Critical patent/EP0485500A1/fr
Application granted granted Critical
Publication of EP0485500B1 publication Critical patent/EP0485500B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, 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
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • Aqueous anionic surfactant concentrates with oleic acid sulfonates as viscosity regulators.
  • the invention relates to aqueous anionic surfactant concentrates containing a) at least 30% by weight, based on the aqueous concentrate, of anionic surfactants from water-soluble salts of
  • Alkylaryl sulfonates alkyl polyglycol ether sulfates, alkylaryl polyglycol ether sulfates, alkyl polyglycol ether sulfosuccinates, alkylaryl polyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates group and b) oleic acid sulfonates.
  • the surfactant content of technical, aqueous anionic surfactant concentrates is usually 30% by weight, based on the total weight of the concentrate. Pastes with a higher surfactant content can only be processed with great difficulty or not at all Process because they are no longer flowable or pumpable at the usual processing temperatures.
  • a special feature of the rheological behavior of these anionic surfactant concentrates is that they do not interfere with the addition of water
  • Viscosity reduction but first react with a thickening to a gel-like state. This results in various problems for further processing, for example in that valves and pipes become blocked, or in that gel clumps formed can only be brought back into solution after mechanical comminution.
  • DE-A 2 251 405 salts of certain carboxylic acids, especially hydroxycarboxylic acids, as viscosity regulators for anionic ones
  • surfactant concentrates are sulfonated aromatic compounds (DE-A 2 305 554), sulfates or sulfonates of aliphatic, optionally substituted hydrocarbons having 1 to 6 carbon atoms (DE-A 2 326 006), cumene sulfonate or acidic phosphoric acid esters (DE-B 16 17 160 ), polyhydric alcohols, carboxylic acids or esters thereof (EP-A 00 08 060), mono- and / or disulfates of polyalkylene ether glycols (EP-B 00 24 711), alkoxylated alcohols (DE-A 37 18 896) and alkali metal alkanesulfonates
  • the invention is directed to aqueous anionic surfactant concentrates which, despite a high anionic surfactant content special viscosity regulators are flowable or processable or have higher solids contents if viscosities are still suitable for processing; the aqueous anionic surfactant concentrates of the invention can also be diluted with water without a significant increase in their viscosity being observed.
  • aqueous anionic surfactant concentrates which a) have at least 30% by weight, based on the aqueous concentrate,
  • Alkylarylsulfonates alkylpolyglycol ether sulfates
  • Alkylaryl polyglycol ether sulfates, alkyl polyglycol ether sulfosuccinates, alkylaryl polyglycol ether sulfosuccinates, alkyl sulfates and alkyl sulfosuccinates group and b) contain oleic acid sulfonates.
  • anionic surfactants contained in the aqueous anionic surfactant concentrates of the invention are known compounds which are described, for example, in J. Falbe (ed.), Surfactants in Consumer Products, pp. 54 to p. 132, Springer Verlag Berlin (1967).
  • Anion surfactants which are particularly preferred in the context of the invention are linear alkylbenzenesulfonates, in particular those having a C 12 -alkyl group, and also alkyl sulfates having 10 to 22 carbon atoms in the (linear) alkyl chains, such as those obtained from lauryl alcohol or stearyl alcohol or technical mixtures thereof, such as coconut oil alcohol or tallow fatty alcohol , are accessible.
  • the oleic acid sulfonates contained in the aqueous anionic surfactant concentrates of the invention as viscosity regulators are compounds which are known from GB-C 1 278 421. You can can be obtained by oleic acid or technical mixtures thereof, as are available from natural, renewable raw materials, in particular beef tallow, sunflower oil, rapeseed oil, olive oil and the like, sulfonated with gaseous sulfur trioxide and the sulfonation products neutralized and hydrolyzed with aqueous bases.
  • the oleic acid sulfonates obtained can contain more or less large proportions of saturated fatty acids and sulfonation products of other unsaturated fatty acids which do not interfere with the action of the oleic acid sulfonates as viscosity regulators.
  • the aqueous anionic surfactants contain linear alkylbenzenesulfonates or alkyl sulfates and oleic acid sulfonates in weight ratios to one another of from 90:10 to 50:50.
  • the invention further relates to the use of the above-mentioned oleic acid sulfonates as viscosity regulators for aqueous anionic surfactant concentrates which contain at least 30% by weight of anionic surfactants from water-soluble salts of alkylarylsulfonates, alkylpolyglycol ether sulfates, alkylarylpolyglycol ether sulfates, alkylpolyglycol ether sulfosuccinates and alkyl etheryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alkyleryl sulfosinate, alky
  • the aqueous anionic surfactant concentrates of the invention can be prepared according to a first process variant by preparing anionic surfactants from the amount of alkyl desired sulfate and alkyl sulfate succinates, the alkyl sulfate and alkyl sulfate succinates, the alkyl sulfate and alkyl sulfate succinate, the alkyl sulfate and alkyl sulfate succinate desired Oleic acid sulfonates, optionally with the addition of water and / or heating, mixes.
  • the aqueous anionic surfactant concentrates of the invention can be prepared by mixing the acid form of the above-mentioned anionic surfactants with the desired amount of oleic acid sulfonates and neutralizing the mixture with concentrated aqueous bases, in particular concentrated aqueous sodium hydroxide solution.
  • the anionic surfactants are alkylarylsulfonates.
  • the other anionic surfactants for example alkyl sulfates, it should be noted that these can be unstable in their acid form, so that they should be neutralized in the presence of the oleic acid sulfonates immediately after their preparation.
  • aqueous anionic surfactant concentrates of the invention despite their content of oleic acid sulfonates, which, based on the anionic surfactants, can be up to 50% by weight, have practically the same surface-active effect as anionic surfactant concentrates without the addition of oleic acid sulfonates.
  • the oleic acid sulfonate sodium salt used was through
  • Gaseous sulfur trioxide produced by heating oleum, was diluted with nitrogen to a concentration of 5% by volume of sulfur trioxide and used in the sulfonation.
  • the oleic acid was applied at a constant rate of 550 g / h.
  • the feed of the sulfur trioxide / nitrogen mixture was adjusted so that the molar ratio of olefinic double bonds present in technical oleic acid (calculated from the iodine number) to sulfur trioxide was 1: 0.9.
  • Reaction temperature of the sulfonation kept at 50 ° C. After leaving the reactor, the reaction mixture was collected in a beaker containing 25% by weight sodium hydroxide solution and then two at a pH of 8 to 9 Heated to 90 ° C for hours. The desired product was obtained in a concentration of 59.5% by weight in water.
  • Table 1 also contains the for comparison purposes
  • aqueous anionic surfactant concentrates of the invention have a significantly reduced viscosity at comparable surfactant concentrations.
  • Oleic acid sulfonate sodium salt Oleic acid sulfonate sodium salt.
  • a commercially available tallow fatty alcohol sulfate (chain distribution: 59 - 66 C 18 , 27 - 35 C 16 , balance: C 12 - C 22 ) was used, which was in the form of a water-containing paste with a content of 55% by weight of detergent substances.
  • the commercial product was dried and then lay as an anhydrous,
  • the dried tallow fatty alcohol sulfate hereinafter referred to as TAS, was treated with an aqueous, 52.8% by weight solution of a
  • Table 2 summarizes the added amounts of TAS, the OS solution and the corresponding amount of OS converted to 100% by weight and water, the weight ratio of TAS to OS obtained and the total content of the solution obtained
  • Tensides (OAS) as well as the viscosities measured in mPas at 60 ° C and 80 ° C according to Höppler on the falling ball viscometer Table 2 also contains the measurement results obtained for comparison with a solution containing only TAS.

Abstract

Des concentrés tensio-actifs anioniques aqueux renfermant (a) au moins 30 % en poids, rapportés au concentré aqueux, de tensio-actifs anioniques appartenant au groupe des sels hydrosolubles des sulfonates d'aryle d'alkyle, sulfates de polyglycoléther d'alkyle, sulfates de polyglycoléther d'aryle d'alkyle, sulfosuccinates de polyglycoléther d'alkyle, sulfosuccinates de polyglycoléther d'aryle d'alkyle, sulfates d'alkyle et sulfosuccinates d'alkyle, et (b) des sulfonates d'acide oléique, présentent, par rapport à des concentrés sans sulfonates d'acide oléique, une viscosité notablement réduite pour une action tensio-active inchangée.
EP90912661A 1989-08-09 1990-07-31 Concentres de tensio-actifs anioniques aqueux avec des sulphonates d'acide oleique comme regulateurs de viscosite Expired - Lifetime EP0485500B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3926345 1989-08-09
DE3926345A DE3926345A1 (de) 1989-08-09 1989-08-09 Waessrige aniontensidkonzentrate mit einem gehalt an oelsaeuresulfonaten sowie die verwendung von oelsaeuresulfonaten als viskositaetsregler fuer waessrige aniontensidkonzentrate
PCT/EP1990/001249 WO1991002045A1 (fr) 1989-08-09 1990-07-31 Concentres de tensio-actifs anioniques aqueux avec des sulphonates d'acide oleique comme regulateurs de viscosite

Publications (2)

Publication Number Publication Date
EP0485500A1 true EP0485500A1 (fr) 1992-05-20
EP0485500B1 EP0485500B1 (fr) 1994-09-21

Family

ID=6386812

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90912661A Expired - Lifetime EP0485500B1 (fr) 1989-08-09 1990-07-31 Concentres de tensio-actifs anioniques aqueux avec des sulphonates d'acide oleique comme regulateurs de viscosite

Country Status (5)

Country Link
EP (1) EP0485500B1 (fr)
JP (1) JPH04506928A (fr)
DE (2) DE3926345A1 (fr)
ES (1) ES2062548T3 (fr)
WO (1) WO1991002045A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7666828B2 (en) 2008-01-22 2010-02-23 Stepan Company Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
US7879790B2 (en) 2008-01-22 2011-02-01 Stepan Company Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them
US7884064B2 (en) 2009-01-21 2011-02-08 Stepan Company Light duty liquid detergent compositions of sulfonated estolides and other derivatives of fatty acids
US7998920B2 (en) 2008-01-22 2011-08-16 Stepan Company Sulfonated estolide compositions containing magnesium sulfate and processes employing them
US8058223B2 (en) 2009-01-21 2011-11-15 Stepan Company Automatic or machine dishwashing compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8119588B2 (en) 2009-01-21 2012-02-21 Stepan Company Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8124577B2 (en) 2009-01-21 2012-02-28 Stepan Company Personal care compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3926345A1 (de) * 1989-08-09 1991-02-14 Henkel Kgaa Waessrige aniontensidkonzentrate mit einem gehalt an oelsaeuresulfonaten sowie die verwendung von oelsaeuresulfonaten als viskositaetsregler fuer waessrige aniontensidkonzentrate
DE4019172A1 (de) * 1990-06-15 1991-12-19 Henkel Kgaa Verwendung von salzen der sulfonierungsprodukte ungesaettigter fettsaeuren als viskositaetsminderer
DE4026639A1 (de) * 1990-08-23 1992-02-27 Henkel Kgaa Waessrige anionische detergensmischungen
DE4107414A1 (de) * 1991-03-08 1992-09-10 Henkel Kgaa Fluessige reinigungsmittel mit einem gehalt an sulfooelsauren disalzen
DE4109250A1 (de) * 1991-03-21 1992-09-24 Henkel Kgaa Verfahren zur herstellung von hochkonzentrierten fettalkoholsulfat-pasten
US5538672A (en) * 1991-08-03 1996-07-23 Henkel Kommanditgesellschaft Auf Aktien Free-flowing water-containing alkyl sulfate pastes
DE4125792A1 (de) * 1991-08-03 1993-02-04 Henkel Kgaa Fliessfaehige waessrige alkylsulfatpasten
DE102007032670A1 (de) 2007-07-13 2009-01-15 Clariant International Ltd. Wässrige Zusammensetzungen enthaltend Alkylpolyethylenglykolethersulfate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3447859A1 (de) * 1984-12-31 1986-07-10 Henkel KGaA, 4000 Düsseldorf Verwendung von alkansulfonaten als viskositaetsregler fuer hochviskose aniontensid-konzentrate
DE3902619A1 (de) * 1989-01-30 1990-08-02 Henkel Kgaa Fluessige reinigungsmittel
DE3926345A1 (de) * 1989-08-09 1991-02-14 Henkel Kgaa Waessrige aniontensidkonzentrate mit einem gehalt an oelsaeuresulfonaten sowie die verwendung von oelsaeuresulfonaten als viskositaetsregler fuer waessrige aniontensidkonzentrate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9102045A1 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7666828B2 (en) 2008-01-22 2010-02-23 Stepan Company Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
US7879790B2 (en) 2008-01-22 2011-02-01 Stepan Company Mixed salts of sulfonated estolides and other derivatives of fatty acids, and methods of making them
US7998920B2 (en) 2008-01-22 2011-08-16 Stepan Company Sulfonated estolide compositions containing magnesium sulfate and processes employing them
US8129328B2 (en) 2008-01-22 2012-03-06 Stepan Company Compositions comprising sulfonated estolides and alkyl ester sulfonates, methods of making them, and compositions and processes employing them
US8338358B2 (en) 2008-01-22 2012-12-25 Stepan Company Compositions comprising sulfonated estolides and alkyl ester sulfonates, methods of making them, and compositions and processes employing them
US7884064B2 (en) 2009-01-21 2011-02-08 Stepan Company Light duty liquid detergent compositions of sulfonated estolides and other derivatives of fatty acids
US8058223B2 (en) 2009-01-21 2011-11-15 Stepan Company Automatic or machine dishwashing compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8119588B2 (en) 2009-01-21 2012-02-21 Stepan Company Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
US8124577B2 (en) 2009-01-21 2012-02-28 Stepan Company Personal care compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof

Also Published As

Publication number Publication date
DE3926345A1 (de) 1991-02-14
DE59007286D1 (de) 1994-10-27
WO1991002045A1 (fr) 1991-02-21
ES2062548T3 (es) 1994-12-16
EP0485500B1 (fr) 1994-09-21
JPH04506928A (ja) 1992-12-03

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