EP0573448B1 - Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree - Google Patents

Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree Download PDF

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Publication number
EP0573448B1
EP0573448B1 EP92903962A EP92903962A EP0573448B1 EP 0573448 B1 EP0573448 B1 EP 0573448B1 EP 92903962 A EP92903962 A EP 92903962A EP 92903962 A EP92903962 A EP 92903962A EP 0573448 B1 EP0573448 B1 EP 0573448B1
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Prior art keywords
alkyl
pastes
alkenyl
carbon atoms
formula
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EP92903962A
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German (de)
English (en)
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EP0573448A1 (fr
Inventor
Andreas Syldath
Karl Schmid
Ditmar Kischkel
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—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
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/662—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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the invention relates to a process for the preparation of alkyl and / or alkenyl sulfate pastes with improved flowability by adding nonionic surfactants as viscosity reducers.
  • Anionic surfactants of the alkyl and alkenyl sulfate type especially those containing alkyl or alkenyl radicals with 16 to 18 carbon atoms, show excellent detergent properties and are suitable for the production of detergents, dishwashing detergents and cleaning agents.
  • alkyl and / or alkenyl sulfates in particular for the production of powdered detergents, has hitherto been limited, since the storage and transportation of aqueous alkyl and / or alkenyl sulfate pastes is associated with serious problems.
  • alkyl and / or alkenyl sulfate pastes have solids contents of 30 to 70 Wt .-% at ambient temperature such a high viscosity and such a strong flow anomaly (rheopexy) that a transfer or pumping is practically impossible.
  • Mixing the pastes with other detergent ingredients also leads to largely inhomogeneous slurries that cannot be processed without problems.
  • WO 91/04313 discloses the use of alkyl polyglucosides as viscosity regulators for alkyl sulfate pastes.
  • EP-A1 0084154 it is proposed to increase the viscosity of aqueous anionic surfactant concentrates by adding higher molecular weight polyethylene glycols.
  • the use of such additives for lowering the viscosity of detergent slurries is also known from World Patent Index, Derwent Publ. Ltd., London, AN 86097588 .
  • the viscosity of alkylarylsulfate, alpha-sulfofatty acid ester and alkyl sulfate pastes can be increased by adding 1 to 15% by weight, based on the surfactant content, of an add-on product from 1 to 15 mol of ethylene and / or propylene oxide to linear or branched, saturated or unsaturated and optionally substituted with further hydroxyl groups alcohols having 8 to 40 carbon atoms are reduced to values below 10,000 mPa.s at 70 ° C.
  • This publication is primarily concerned with the viscosity control of alpha-sulfofatty acid ester salt pastes.
  • the object of the invention was therefore to provide a process for the preparation of alkyl and / or alkenyl sulfate pastes with improved flow properties which is free from the disadvantages described.
  • the selected nonionic surfactants to be used by the process according to the invention not only reduce the viscosity of alkyl and / or alkenyl sulfate pastes so much even at low temperatures that pumping around is possible without the risk of chemical decomposition, but also that Eliminate flow anomaly, which is a significant relief for the design of delivery pumps and delivery routes for the alkyl and / or alkenyl sulfate pastes.
  • the invention includes the knowledge that the addition of the nonionic surfactants makes it possible to produce homogeneous detergent slurries.
  • the washing, rinsing and cleaning ability of the alkyl and / or alkenyl sulfate pastes is not negatively influenced in the sense of the process according to the invention by the addition of the nonionic surfactants.
  • the pastes can be sprayed without pluming problems.
  • polyethylene glycol ethers with a narrow homolog distribution have proven to be particularly advantageous.
  • Alkyl and alkenyl sulfates are known anionic surfactants which can be obtained by the usual methods of preparative organic chemistry. As a rule, they are produced by the reaction of saturated and / or unsaturated, aliphatic primary alcohols with sulfur trioxide. Alkyl and / or alkenyl sulfates to which the process according to the invention extends are derived from fatty alcohols having 10 to 22 carbon atoms.
  • Typical examples of this are carpinal alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol or erucyl alcohol.
  • alkyl sulfates which are derived from saturated fatty alcohols having 12 to 18, in particular 16 to 18, carbon atoms.
  • the alkyl and / or alkenyl sulfates can also be derived from technical alcohol cuts, such as z. B. in the hydrogenation of technical fatty acid methyl ester mixtures of natural origin or of aldehydes from Roelen's oxosynthesis.
  • Alkyl and / or alkenyl sulfates based on technical coconut or tallow alcohol cuts are preferred. These include such primary fatty alcohols to understand, which on average have the following C chain distribution according to Table 1: Table 1 C chain distribution of preferred fatty alcohols C number Coconut alcohol % by weight Tallow alcohol % by weight 10th 0-3 12th 48-58 14 19-24 0-3 16 9-12 45-55 18th 11-14 45-55 20th 0-3
  • Non-ionic surfactants which follow the formula (II) can be used as the alkyl polyethylene glycol ether (component a) in the process according to the invention: R2O- (CH2CH2O) n H (II) in which R2 is a linear C 12/14 and / or C 12/18 alkyl radical and n is a number from 2 to 7.
  • alkyl polyethylene glycol ethers of the formula (II) in which R2 is a linear C 12/14 and / or C 12/18 alkyl radical and n is a number from 5 to 7.
  • alkyl polyethylene glycol ethers of the formula (II) can be used, the residual alcohol content of which, for example by distillation, has been reduced to a content of less than 1% by weight, based on the nonionic surfactant.
  • Possible components b) are alkylpolypropylene glycol ethers of the formula (III) in which R3 is a linear alkyl radical having 10 to 18 carbon atoms and m is a number from 1 to 4.
  • R3 is a linear alkyl radical having 10 to 18 carbon atoms and m is a number from 1 to 3.
  • Mixed ethers of the formula (IV) are suitable as component c) in which R4 represents an alkyl or alkenyl radical having 6 to 22 carbon atoms, R5 represents an alkyl radical with 1 to 4 carbon atoms or a benzyl radical, R6 represents hydrogen or a methyl group and y represents numbers from 1 to 10.
  • R4 represents an alkyl radical having 12 to 18 carbon atoms
  • R5 is a butyl or benzyl radical
  • R6 is hydrogen and y is a number from 4 to 10.
  • Hydroxy mixed ethers of the formula (V) are finally suitable as component d), into consideration, in which R7 represents an alkyl radical having 6 to 16 carbon atoms, R8 represents an alkyl radical having 1 to 4 carbon atoms or a benzyl radical, R9 represents hydrogen or is a methyl group and z represents numbers from 1 to 10.
  • R7 represents an alkyl radical having 8 to 10 carbon atoms
  • R8 is a butyl or benzyl radical
  • R9 is hydrogen and z is a number from 4 to 10.
  • nonionic surfactants are known compounds, the preparation of which - unless stated otherwise - is, for. B. in J. Falbe, U. Hasserodt (ed.), "Catalysts, surfactants and mineral oil additives , Thieme Verlag, Stuttgart, 1978 or J. Falbe (ed.)” Surfactants in Consumer Products ", Springer Verlag, Berlin, 1986 is.
  • the nonionic surfactants can be added to the alkyl and / or alkenyl sulfate pastes individually or in combinations, the mixing ratio being able to vary over a wide range.
  • the use of a mixture containing polyglycol ethers, in particular alkyl polyethylene glycol ether, and alkyl glucosides in a weight ratio of 10:90 to 90:10, whose free alcohol content is less than 1% by weight, based on the mixture has proven particularly advantageous.
  • the nonionic surfactants can the alkyl and / or alkenyl sulfates in amounts of 1 to 15, preferably 5 to 12 wt .-% - based on the solids content of the Pastes - either added during or after neutralization.
  • the alkyl and / or alkenyl polyethylene glycol ether (component a) has proven to be particularly advantageous to use these nonionic surfactants in amounts of 5 to 12, in particular 7.5 to 10,% by weight, based on the solids content of the pastes.
  • alkyl and / or alkenyl sulfates can be mixed with the nonionic surfactants by mechanical means, for example by stirring or pumping, if appropriate at temperatures from 55 to 70 ° C .; there is no chemical reaction between the components.
  • the anionic surfactant content and the unsulfonated contents were determined according to the DGF standard methods, Stuttgart, 1950-1984, H-III-10 and G-II-6b.
  • the sulfate content was calculated as sodium sulfate, the water content was determined according to the Fischer method.
  • Viscosities (specified in mPa.s) E.g N c (N) % Temperature (° C) 75 70 65 60 55 1 A 5.0 3,500 3,500 4,500 7,500 14,500 7.5 2,750 3,000 3,500 5,500 12,000 10.0 2,250 2,250 3,250 3,500 5,250 2nd B 5.0 3,500 3,500 4,500 7,500 14,500 7.5 3,000 3,250 3,750 5,750 13,250 10.0 3,000 3,250 3,500 6,500 11,000 3rd C.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Claims (5)

  1. Procédé de production de pâtes de sulfate d'alkyle et/ou d'alcényle à fluidité améliorée, caractérisé en ce que l'on additionne à des pâtes aqueuses de sulfates d'alkyle et/ou d'alcényle de la formule (I)



            R¹O-SO₃X   (I)



    dans laquelle R¹ représente un radical alkyle et/ou alcényle comportant 10 à 22 atomes de carbone et X correspond à un métal alcalin ou alcalino-terreux, qui présentent une proportion de matière solides de 30 à 70 % en poids, au moins un tensioactif non ionique sélectionné parmi le groupe constitué des
    a) alkylpolyéthylèneglycoléthers de la formule (II),



            R²O-(CH₂CH₂O)nH   (II)



       dans laquelle R² représente un radical alkyle linéaire en C12/14 et/ou en C12/18, et n correspond à un nombre de 2 à 7,
    b) alkylpolypropylèneglycoléthers de la formule (III),
    Figure imgb0011
        dans laquelle R³ représente un radical alkyle linéaire comportant 10 à 18 atomes de carbone et m correspond à un nombre de 1 à 4,
    c) éthers mixtes et/ou
    d) hydroxyéthers mixtes,
    à la suite de quoi il s'instaure une viscosité des pâtes de sulfate d'alkyle et/ou d'alcényle de maximum 15.000 mPa.s à 55 °C (Brookfield, broche 6, 20 tours/min).
  2. Procédé selon la revendication 1, caractérisé en ce que l'on met en oeuvre des sulfates d'alkyle de la formule (I), dans laquelle R¹ représente un radical alkyle comportant 16 à 18 atomes de carbone et X correspond au sodium.
  3. Procédé selon les revendications 1 et 2, caractérisé en ce que l'on met en oeuvre comme composant (c), des éthers mixtes de la formule (IV)
    Figure imgb0012
        dans laquelle R⁴ représente un radical alkyle ou alcényle comportant 6 à 22 atomes de carbone, R⁵ correspond à un radical alkyle comportant 1 à 4 atomes de carbone ou à un radical benzyle, R⁶ est l'hydrogène ou un groupe méthyle et y représente un nombre de 1 à 10.
  4. Procédé selon les revendications 1 et 2, caractérisé en ce que l'on met en oeuvre comme composant (d), des hydroxyéthers mixtes de la formule (V)
    Figure imgb0013
        dans laquelle R⁷ représente un radical alkyle comportant 6 à 16 atomes de carbone, R⁸ correspond à un radical alkyle comportant 1 à 4 atomes de carbone ou à un radical benzyle, R⁹ est l'hydrogène ou un groupe méthyle et z représente un nombre de 1 à 10.
  5. Procédé selon les revendications 1 à 4, caractérisé en ce que l'on additionne les tensioactifs non ioniques aux pâtes de sulfate d'alkyle et/ou d'alcényle, en proportions de 1 à 15 % en poids par rapport à la concentration en matières solides.
EP92903962A 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree Expired - Lifetime EP0573448B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4105851A DE4105851A1 (de) 1991-02-25 1991-02-25 Verfahren zur herstellung von alkyl- und/oder alkenylsulfat-pasten mit verbesserter fliessfaehigkeit
DE4105851 1991-02-25
PCT/EP1992/000330 WO1992014809A1 (fr) 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree

Publications (2)

Publication Number Publication Date
EP0573448A1 EP0573448A1 (fr) 1993-12-15
EP0573448B1 true EP0573448B1 (fr) 1995-06-14

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EP92903962A Expired - Lifetime EP0573448B1 (fr) 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree

Country Status (7)

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EP (1) EP0573448B1 (fr)
JP (1) JPH06505042A (fr)
AT (1) ATE123801T1 (fr)
DE (2) DE4105851A1 (fr)
DK (1) DK0573448T3 (fr)
ES (1) ES2073288T3 (fr)
WO (1) WO1992014809A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4232166A1 (de) * 1992-09-25 1994-03-31 Henkel Kgaa Fließfähige wäßrige Alkylsulfatpasten
DE4241473A1 (de) * 1992-12-09 1994-06-16 Henkel Kgaa Wasserlösliche Tensidgemische für Flüssigwaschmittel
DE4403323A1 (de) * 1993-09-23 1995-08-10 Henkel Kgaa Extrudierte Wasch- oder Reinigungsmittel mit verbesserten Löseeigenschaften
DE19519889A1 (de) † 1995-05-31 1996-12-05 Henkel Kgaa Verfahren zur Herstellung hellfarbiger, niedrigviskoser Alkyloligoglycoside
DE19526483A1 (de) * 1995-07-20 1997-01-23 Henkel Kgaa Tensidabmischungen mit verbesserter Löslichkeit von Aniontensiden auf Basis langkettiger Alkylsulfatsalze auch bei niederen Flottentemperaturen
US20020073770A1 (en) 1998-10-08 2002-06-20 Norbert Diekhans Device and method for measuring the moisture of crop material in agricultural machines
DE19908563C2 (de) * 1999-02-27 2002-11-14 Cognis Deutschland Gmbh Reinigungsmittel für harte Oberflächen
DE10046363A1 (de) * 2000-09-20 2002-03-28 Cognis Deutschland Gmbh Fließfähige wässrige Fettalkoholsulfatpasten
DE102004015392A1 (de) * 2004-03-26 2005-10-20 Henkel Kgaa Maschinelles Geschirrspülmittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3151679A1 (de) * 1981-12-28 1983-07-07 Henkel KGaA, 4000 Düsseldorf "verwendung von viskositaetsreglern fuer tensidkonzentrate"
DE3305430A1 (de) * 1983-02-17 1984-08-23 Henkel KGaA, 4000 Düsseldorf Verwendung von alkoholen und deren derivaten als viskositaetsregler fuer hochviskose technische tensid-konzentrate
DE3577878D1 (de) * 1984-11-06 1990-06-28 Henkel Kgaa Monoglykoside als viskositaetsregler in detergenzien.
DE3630533A1 (de) * 1986-09-08 1988-03-10 Henkel Kgaa Neue tensidgemische und ihre verwendung
WO1991004313A1 (fr) * 1989-09-14 1991-04-04 Henkel Corporation Compositions tensio-actives anioniques et amphoteres a viscosite reduite

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Publication number Publication date
ATE123801T1 (de) 1995-06-15
DK0573448T3 (da) 1995-10-16
EP0573448A1 (fr) 1993-12-15
DE59202552D1 (de) 1995-07-20
WO1992014809A1 (fr) 1992-09-03
DE4105851A1 (de) 1992-08-27
JPH06505042A (ja) 1994-06-09
ES2073288T3 (es) 1995-08-01

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