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WO1992007054A1 - Procede de production de pates en sulfate d'alkyle a fluidite amelioree - Google Patents

Procede de production de pates en sulfate d'alkyle a fluidite amelioree Download PDF

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Publication number
WO1992007054A1
WO1992007054A1 PCT/EP1991/001912 EP9101912W WO9207054A1 WO 1992007054 A1 WO1992007054 A1 WO 1992007054A1 EP 9101912 W EP9101912 W EP 9101912W WO 9207054 A1 WO9207054 A1 WO 9207054A1
Authority
WO
WIPO (PCT)
Prior art keywords
pastes
weight
fatty acid
alkyl sulfate
sulfonation products
Prior art date
Application number
PCT/EP1991/001912
Other languages
German (de)
English (en)
Inventor
Bernd Fabry
Rainer Hofmann
Martina Kihn-Botulinski
Frank Wangemann
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP3515951A priority Critical patent/JPH06501726A/ja
Publication of WO1992007054A1 publication Critical patent/WO1992007054A1/fr

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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols

Definitions

  • the invention relates to a process for producing alkyl sulfate pastes with improved flow properties by adding sulfonation products of unsaturated fatty acid glyceride esters as viscosity reducers.
  • Anionic surfactants of the alkyl sulfate type in particular those which contain alkyl radicals with 16 to 18 carbon atoms, have excellent detergent properties and are used in particular in powder detergents.
  • aqueous alkyl sulfate pastes are used as the starting point.
  • the aqueous surfactant pastes have the highest possible solids content.
  • alkyl sulfate pastes can only be concentrated up to a certain solids content. Above this limit, the viscosity generally reaches such high values that the pumpability of the surfactant solutions is no longer guaranteed, even at elevated temperatures.
  • Alkoxylated alcohols [DE-A-37 18 896] or aliphatic hydrocarbons [DD-A-240 025] are suitable for lowering the viscosity of alkylbenzenesulfonate pastes.
  • Viscosity reducers are sulfonated aromatic compounds [DE-A-23 05 554], cumene sulfonate or acidic phosphoric acid esters [DE-B-16 17 160], polyhydric alcohols, carboxylic acids or esters thereof [EP-A-0008060] or Mono- and / or disulfates of polyalkylene glycol ethers [EP-B-0024711].
  • the object of the invention was therefore to provide a process for the production of alkyl sulfate pastes with improved flow properties.
  • the invention relates to a process for the preparation of alkyl sulfate pastes with improved flow properties, which is characterized in that alkyl sulfate pastes with solids contents of 30 to 80% by weight of sulfonation products of unsaturated fatty acid glyceride esters in amounts of 1 to 50% by weight, based on the solids content of the pastes.
  • alkyl sulfate pastes is sufficient at room temperature in order to significantly reduce the viscosity and the yield point.
  • the invention includes the knowledge that the after Characterized alkyl sulfate pastes produced according to the invention in spray drying by an improved conveyability and a lower energy requirement.
  • Alkyl sulfates are known anionic surfactants that can be obtained by the usual methods of preparative organic chemistry. As a rule, they are produced by the reaction of aliphatic primary alcohols with sulfur trioxide. Alkyl sulfates to which the process according to the invention extends are derived from fatty alcohols having 12 to 22 carbon atoms. Typical examples of this are lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or behenyl alcohol. A particularly drastic reduction in the paste viscosity is observed in alkyl sulfates which are derived from fatty alcohols having 12 to 18, in particular 16 to 18, carbon atoms.
  • the alkyl sulfates can also be derived from technical alcohol cuts, such as those obtained in the hydrogenation of technical fatty acid methyl ester mixtures of natural origin or from aldehydes from Roelen's oxosynthesis. Alkyl sulfates based on technical coconut or tallow alcohol cuts are preferred. These are to be understood as primary fatty alcohols which on average have the following C chain distribution:
  • the sulfonation products of unsaturated fatty acid glyceride esters to be added to the alkyl sulfate pastes in the context of the invention are compounds which are obtained by reacting unsaturated mono-, di- and / or triglycerides with sulfonating agents, in particular gaseous sulfur trioxide and subsequent neutralization and hydrolysis of the reaction products formed .
  • sulfonating agents in particular gaseous sulfur trioxide and subsequent neutralization and hydrolysis of the reaction products formed .
  • a method for producing such compounds is described, for example, in German patent DE-A-1246717.
  • the glycerides can be of natural or synthetic origin and have iodine numbers from 60 to 210, preferably 100 to 130.
  • the fatty acid component of the glycerides can also contain 16 to 22 carbon atoms and 1, 2 or 3 double bonds.
  • Examples include the sulfonation products of the glycerides of palmitoleylic acid, oleic acid, elaidyl acid, petroselic acid, ricinoleic acid, linoleic acid, linolenic acid or erucic acid.
  • the sulfonation products can also be derived from technical glycerol mixtures, such as, for example, rape oil, sunflower oil, olive oil, peanut oil, coriander oil, cottonseed oil, castor oil or fish oil.
  • the fatty acid component of the sulfonated fatty acid glyceride esters can also contain fractions of saturated fatty acids with 6 to 22 carbon atoms.
  • the viscosity-reducing influence is exerted by sulfonation products of unsaturated fatty acid glyceride esters, which are obtained by reacting new oleic rape oil with 1.0 to 1.3 moles of sulfur trioxide per mole of glyceride at temperatures of 50 to 90 ° C. and subsequent neutralization and hydrolysis with aqueous Receives sodium hydroxide solution.
  • the sulfonation products of unsaturated fatty acid glyceride esters are complex mixtures since the glycerides can react with the sulfonating agent in a variety of ways. Addition products of S03 to the olefinic double bond as well as various glyceride sulfates are created. It also contains fractions of soaps and sulfated soaps.
  • the sulfonation products of the unsaturated fatty acid glyceride esters can be added to the alkyl sulfate either during or after the neutralization. It is also possible to mix the acidic sulfuric acid half-ester with an acidic sulfonation product of an unsaturated fatty acid glyceride and to neutralize both substances together.
  • the sulfonation products are added to the alkyl sulfate pastes in amounts of 1 to 50% by weight, based on the solids content of the paste.
  • the alkyl sulfate pastes 5 to 30, preferably 10 to 20% by weight, based on the solids content of the paste to add the sulfonation products.
  • the alkyl sulfate pastes are mixed with the sulfonation products mechanically, for example by stirring or pumping optionally elevated temperature of 40 to 70 ° C; there is no chemical reaction between the components.
  • Anionic surfactant content 49.8% by weight Unsulfated components 4.0% by weight Sodium sulfate 1.4% by weight water 44.8% by weight
  • the product was then adjusted to a pH of 6.8 using hydrochloric acid and buffered with 1% by weight, based on the solids content, of citric acid.
  • Anionic surfactant content 20.0% by weight Unsulfated components 58.1% by weight sodium sulfate 2.1% by weight water 19.8% by weight
  • the anionic surfactant content (WAS) and the unsulfonated contents (US) were determined according to the DGF standard methods, Stuttgart, 1950-1984, H-111-10 and G-II-6b.
  • the sulfate content was calculated as sodium sulfate, the water content was determined by the Fischer method.

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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)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

On obtient des pâtes en sulfate d'alkyle ayant une fluidité améliorée en ajoutant à des pâtes en sulfate d'alkyle ayant une teneur en matières solides comprise entre 30 et 80 % en poids des quantités de produits de la sulfonation d'esters glycérides d'acides gras insaturés comprises entre 1 et 50 % en poids, par rapport à la teneur en matières solides des pâtes.
PCT/EP1991/001912 1990-10-17 1991-10-08 Procede de production de pates en sulfate d'alkyle a fluidite amelioree WO1992007054A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP3515951A JPH06501726A (ja) 1990-10-17 1991-10-08 流動性を改良したアルキルスルフェートペーストの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4032910.0 1990-10-17
DE4032910A DE4032910A1 (de) 1990-10-17 1990-10-17 Verfahren zur herstellung von alkylsulfatpasten mit verbesserten fliesseigenschaften

Publications (1)

Publication Number Publication Date
WO1992007054A1 true WO1992007054A1 (fr) 1992-04-30

Family

ID=6416441

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/001912 WO1992007054A1 (fr) 1990-10-17 1991-10-08 Procede de production de pates en sulfate d'alkyle a fluidite amelioree

Country Status (4)

Country Link
EP (1) EP0553147A1 (fr)
JP (1) JPH06501726A (fr)
DE (1) DE4032910A1 (fr)
WO (1) WO1992007054A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993003128A1 (fr) * 1991-08-03 1993-02-18 Henkel Kommanditgesellschaft Auf Aktien Pates aqueuses fluides de sulfate d'alkyle
WO1993025646A1 (fr) * 1992-06-17 1993-12-23 Lion Corporation Composition detergente peu agressive pour la peau
WO1994007975A1 (fr) * 1992-09-25 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Pates de sulfate d'alkyle aqueuses coulantes
US5538672A (en) * 1991-08-03 1996-07-23 Henkel Kommanditgesellschaft Auf Aktien Free-flowing water-containing alkyl sulfate pastes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19714043C2 (de) * 1997-04-05 2002-09-26 Cognis Deutschland Gmbh Verwendung von Glycerinsulfaten als Viskositätsregulatoren für konzentrierte wäßrige Alkyl(ether)sulfatpasten

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024711A1 (fr) * 1979-09-01 1981-03-11 Henkel Kommanditgesellschaft auf Aktien Produits concentrés de tensides aqueux et procédé pour l'amélioration des propriétés d'écoulement de produits concentrés de tensides aqueux difficilement transportables
EP0178557A1 (fr) * 1984-10-12 1986-04-23 Henkel Kommanditgesellschaft auf Aktien Procédé pour la fabrication d'agents de graissage pour cuir et fourrures
WO1991009009A1 (fr) * 1989-12-15 1991-06-27 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de sels d'esters sulfones d'acides gras et de glycerine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024711A1 (fr) * 1979-09-01 1981-03-11 Henkel Kommanditgesellschaft auf Aktien Produits concentrés de tensides aqueux et procédé pour l'amélioration des propriétés d'écoulement de produits concentrés de tensides aqueux difficilement transportables
EP0178557A1 (fr) * 1984-10-12 1986-04-23 Henkel Kommanditgesellschaft auf Aktien Procédé pour la fabrication d'agents de graissage pour cuir et fourrures
WO1991009009A1 (fr) * 1989-12-15 1991-06-27 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de sels d'esters sulfones d'acides gras et de glycerine

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993003128A1 (fr) * 1991-08-03 1993-02-18 Henkel Kommanditgesellschaft Auf Aktien Pates aqueuses fluides de sulfate d'alkyle
US5538672A (en) * 1991-08-03 1996-07-23 Henkel Kommanditgesellschaft Auf Aktien Free-flowing water-containing alkyl sulfate pastes
WO1993025646A1 (fr) * 1992-06-17 1993-12-23 Lion Corporation Composition detergente peu agressive pour la peau
US5681803A (en) * 1992-06-17 1997-10-28 Lion Corporation Detergent composition having low skin irritability
WO1994007975A1 (fr) * 1992-09-25 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Pates de sulfate d'alkyle aqueuses coulantes

Also Published As

Publication number Publication date
DE4032910A1 (de) 1992-04-23
JPH06501726A (ja) 1994-02-24
EP0553147A1 (fr) 1993-08-04

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