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WO1992000274A1 - Sulfates d'ether d'octadienyle - Google Patents

Sulfates d'ether d'octadienyle Download PDF

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Publication number
WO1992000274A1
WO1992000274A1 PCT/EP1991/001163 EP9101163W WO9200274A1 WO 1992000274 A1 WO1992000274 A1 WO 1992000274A1 EP 9101163 W EP9101163 W EP 9101163W WO 9200274 A1 WO9200274 A1 WO 9200274A1
Authority
WO
WIPO (PCT)
Prior art keywords
octadienyl
ether sulfates
octadienyl ether
formula
sulfonation
Prior art date
Application number
PCT/EP1991/001163
Other languages
German (de)
English (en)
Inventor
Bernd Fabry
Bert Gruber
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
Publication of WO1992000274A1 publication Critical patent/WO1992000274A1/fr

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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
    • 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

  • the invention relates to octadienyl ether sulfates obtainable by sulfonating octadienyl ethers and subsequent neutralization and hydrolysis of the reaction products with aqueous bases, a process for their preparation and their use as surface-active agents.
  • fatty alkyl sulfates Sulfation products of fatty alcohols
  • fatty alcohol ethoxylates fatty alkyl ether sulfates
  • fatty alkyl ether sulfates Sulfation products of fatty alcohols
  • fatty alkyl ether sulfates Sulfation products of fatty alcohols
  • fatty alcohol ethoxylates fatty alkyl ether sulfates
  • the fatty alkyl sulfates and fatty alkyl ether sulfates show an insufficient solubility in cold water and an unsatisfactory foaming power.
  • One possibility of obtaining products with improved water solubility is to include unsaturated fatty alcohols in the sulfation. add [J.Aa.Oil.Che ⁇ .Soc. 36, 241 (1959)].
  • alkenyl sulfates are generally only accessible in the C chain range 16 to 22 and also have little storage stability.
  • the object of the invention was therefore to develop new ether sulfates which have a higher solubility in cold water and an improved foaming power and are free from the disadvantages described.
  • the invention relates to octadienyl ether sulfates of the formula (I)
  • R * stands for an aliphatic hydrocarbon radical with 8 carbon atoms and 2 double bonds
  • R 2 for hydrogen or a methyl group
  • n for numbers from 1 to 10
  • X for hydrogen, an alkali metal, alkaline earth metal, ammonium or amine radical.
  • the invention includes the knowledge that the octadienyl ether sulfates are readily soluble in cold water, have a high foaming power and are storage rod 1.
  • Octadienyl ether sulfates with particularly advantageous properties are obtained when in formula (I) R 2 is hydrogen, n is a number from 1 to 6 and X is an alkali metal, in particular sodium.
  • the invention further relates to a process for the preparation of octadienyl ether sulfates of the formula (I),
  • R * represents an aliphatic hydrocarbon radical with 8 carbon atoms and 2 double bonds
  • R 2 represents hydrogen or a methyl group
  • n represents numbers from 1 to 10
  • X represents hydrogen, an alkali metal, alkaline earth metal, ammonium or amine radical
  • R 1 , R 2 and n have the meanings given above, and subsequent neutralization and hydrolysis of the reaction products with aqueous bases.
  • Octadienyl ethers in which R 2 is hydrogen and n is a number from 1 to 6 are particularly suitable for the production of octadienyl ether sulfates with particularly good performance properties.
  • Octadienyl ethers of the formula (II), which can be used as starting material in the sense of the invention, are obtained by transition metal-catalyzed telomerization of 1,3-butadiene with Gly- obtained colethers [J.Mol.Catal. JO-247 (1981) Organomet. 5, 473, 514 (1986)].
  • glycol component of the octadienyl ethers are, for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,2-butanediol and addition products of on average 1 to 10 mol of ethylene and / or propylene oxide (in random or block distribution) of glycol ethers which can have a customary or narrow homolog distribution.
  • the octadienyl ethers can be sulfonated using customary sulfonating agents, for example sulfuric acid, oleu, chlorosulfonic acid or amidosulfonic acid.
  • customary sulfonating agents for example sulfuric acid, oleu, chlorosulfonic acid or amidosulfonic acid.
  • the sulfonation with gaseous sulfur trioxide is carried out in the manner known for fatty acid low alkyl esters [J.Falbe (ed.). "Surfactants in consumer products", Springer Verlag, Berlin-Heidelberg, 1987, pp. 61-63], with reactors that work according to the falling film principle being preferred.
  • the sulfur trioxide is diluted with an inert gas, preferably air or nitrogen, and used in the form of a gas mixture which contains the sulfonating agent in a concentration of 1 to 8, in particular 2 to 5,% by volume.
  • the molar ratio of the octadienyl ether to the gaseous sulfur trioxide is 1: 0.95 to 1: 1.5.
  • operating conditions of 1: 1.05 to 1: 1.3 have proven to be optimal.
  • the sulfonation is carried out at temperatures from 35 to 80, it being possible for octadienyl ethers, which contain a number from 1 to 5 ethylene or propylene oxide units, to be reacted within the stated limits at low temperatures of 35 to 50 ° C., while starting materials are used higher degrees of alkoxylation due to their rheological behavior require higher reaction temperatures of 50 to 80 ° C.
  • the acidic sulfonation products obtained during the sulfonation are stirred into aqueous bases, neutralized and adjusted to a pH of 6.5 to 8.5.
  • bases for the neutralization come alkali metal hydroxides such as sodium, potassium and lithium hydroxide, alkaline earth metal oxides and hydroxides such as magnesium oxide, magnesium hydroxide, calcium oxide and calcium hydroxide, ammonia, mono-, di- and tri-C2-4-alkanolamines, for example Mono-, di- and triethanolamine as well as primary, secondary or tertiary C 1-4 alkylamines into consideration.
  • the neutralization bases are preferably used in the form of 5 to 55% by weight aqueous solutions, 5 to 25% by weight aqueous sodium hydroxide solutions being preferred.
  • the sulfation of the octadienyl ether primarily involves sulfation of the free hydroxyl function, resulting in compounds which follow the formula (I).
  • an electrophilic addition of sulfur trioxide molecules to the double bonds can also take place as a side reaction.
  • the primarily formed sultones are not thermodynamically stable and decompose over time to form sulfonic acids, which greatly reduce the pH of the aqueous solutions of the octadienyl ether sulfates and can contribute to their decomposition.
  • the octadienyl ether sulfates must be neutralized in the presence of excess base over a period of 0.1 to 6, preferably 2 to 4
  • the sulfonation products can be added in a known manner by adding hydrogen peroxide or
  • Sodium hypochlorite solution to be bleached. Based on the solids content in the solution of the sulfonation products, 0.2 to 2% by weight of hydrogen peroxide, calculated as a 100% substance, or corresponding amounts of sodium hypochlorite are used.
  • the pH of the solutions can be adjusted using suitable buffering agents, e.g. B. be kept constant with sodium phosphate or citric acid. To stabilize against bacterial attack, conservation is also recommended, e.g. B. with formaldehyde solution, p-hydroxybenzoate, sorbic acid or other known preservatives.
  • the octadienyl ether sulfates are distinguished by a marked reduction in the surface tension of the water and promote the wetting of solid interfaces with water. They are also suitable for emulsifying oils and fats in aqueous systems.
  • the invention therefore also relates to the use of the octadienyl ether sulfates as surface-active agents and for the preparation of powder detergents, liquid detergents, dishwashing detergents, cleaning agents for hard surfaces, hair shampoos and the like, in which they are used in amounts of 0.1 to 25, preferably 1 to 10% by weight, based on the solids content l of the products, may be present.
  • the products A to E were distilled, parts of octatria, which was formed as a by-product, being separated off.
  • the distilled octadienyl ethers were then used in the sulfation.
  • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On obtient des sulfates d'éther d'octadiényle ayant un haut pouvoir moussant et une bonne solubilité dans de l'eau froide par sulfonation d'éthers d'octadiényle obtenus par télomérisation de butadiène avec des éthers de glycol, suivie de la neutralisation et de l'hydrolyse des produits de la réaction avec des bases aqueuses.
PCT/EP1991/001163 1990-06-30 1991-06-22 Sulfates d'ether d'octadienyle WO1992000274A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4020973.3 1990-06-30
DE4020973A DE4020973A1 (de) 1990-06-30 1990-06-30 Octadienylethersulfate

Publications (1)

Publication Number Publication Date
WO1992000274A1 true WO1992000274A1 (fr) 1992-01-09

Family

ID=6409470

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/001163 WO1992000274A1 (fr) 1990-06-30 1991-06-22 Sulfates d'ether d'octadienyle

Country Status (2)

Country Link
DE (1) DE4020973A1 (fr)
WO (1) WO1992000274A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0300444A1 (fr) * 1987-07-24 1989-01-25 Henkel Kommanditgesellschaft auf Aktien Mélanges de sulfates d'alkyle et de sulfate d'ether et leur utilisation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0300444A1 (fr) * 1987-07-24 1989-01-25 Henkel Kommanditgesellschaft auf Aktien Mélanges de sulfates d'alkyle et de sulfate d'ether et leur utilisation

Also Published As

Publication number Publication date
DE4020973A1 (de) 1992-01-02

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