Classifications

• • 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
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
• • 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
• • 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
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
  • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
  • Y10S516/03—Organic sulfoxy compound containing

Definitions

• Acid sulfates corresponding to the formula C H OCH CH OSO OI-I are known in the art. They may for example be pre pared by condensing lauryl alcohol with ethylene oxide and sulfating the product thus obtained. In this process one generally starts from technically pure lauryl alcohol and uses the ethylene oxide in an amount corresponding to the desired average number of ethoxy groups. Accordingly mixtures are usually obtained in which about 25% of the compounds contain instead of the dodecyl radical another alkyl radical having from 8-16 carbon atoms, whilst the value of n may vary rather widely for the individual compounds in the mixture. These compounds upon neutralization with sodium hydroxide yield neutral salts having a very good surface-active activity. Vide in this respect Soap, Perfumery and Cosmetics, December 1956, page 1367 and Soap and Chemical Specialties, August 1956, page 45.
• a further object of the invention is to provide useful methods for making such salts.
• novel salts of compounds of the formula C H OCH CH OSO OH in which n has an average value from 2 to 3 and the dodecyl radical may be replaced partly by other alkyl radicals having from 8 to 16 carbon atoms and an amine chosen from the group of diethylamine, isopropylamine and butylethanolamine in anhydrous state are liquid under normal conditions of temperature and pressure.
• salts may be obtained by neutralizing compounds of the formula C H OCH CH OSO OH in which n has an average value of from 2 to 3 and the dodecyl radical may be partly replaced by other alkyl radicals having from 8-16 carbon atoms with an amine from the group of diethylamine, isopropylamine, butylethanolamine and mixtures thereof.
• the neutralization may be carried out by adding the amine to the acid sulfates or alternatively by adding the acid sulfates to the amine. Diethylamine and isopropylamine are rather volatile substances, so that losses in these amines may occur as a result of the heat of the reaction generated at the surface. In these cases therefore we prefer to introduce the amine below the surface of the acid sulfate. It is of course advantageous to stir during the neutralization step. If desired the neutralization may be carried out with refluxing or in a closed system under a superatmospheric pressure.
• the neutralization is carried out preferably at temperatures somewhat above room temperature, e.g. at 30 C., because the viscosity of the mixtures is somewhat lower at such temperatures, which facilitates stirring.
• the required amount of amine may easily be determined beforehand or during the neutralization by simple experiments. As the starting products are strongly acidic and the amines used are not strong bases, the amount of the latter is always greater than the equivalent amount based on the amount of the acid sulfates.
• novel products of our invention have in aqueous solution the same surface-active properties as the corresponding sodium salts, but then moreover have the advantage of being liquid in anhydrous conditions. This property makes it possible to deliver them in undiluted state to the buyer, which means an important saving in transport cost.
• the products of our invention dissolve Well in Water. The dissolution rate may of course be increased by heating. However, a fast dissolution takes place already at room temperature upon the addition of various compounds, such as alcohol, glycols and salts, to the products of our invention. For example, the products of our invention dissolve at sufficient rate at room temperature in a l-percent sodium chloride solution.
• the products of our invention are liquid in anhydrous condition moreover renders them suitable for a number of other uses.
• they may be used as such as a shampoo in which case they are diluted by the user on the scalp with warm water.
• the novel products of our invention may also be used as emulsifiers in non-aqueous systems, e.g. in non-aqueous insecticidal compositions.
• Example I An acid sulfate was prepared by condensing a technical grade lauryl alcohol with 2.2 mols of ethylene oxide and sulfating the condensation product. 100 g. of this acid sulfate were neutralized by adding diethylamine in portions beneath the surface of the acid sulfate. During the neutralization the temperature was maintained below 30 C. by cooling. After the equivalent amount of amine has been added, the neutralization reaction was followed by taking at regular intervals samples of the reaction mixture, making a concentrated aqueous solution of these samples and exaluating the pH of these solutions. In this way so much of the amine was added that the pH of the aqueous solution was about 7. A total amount of 27.2 g. of diethyl amine was required to that effect.
• Example II An acid sulfate was prepared in the manner disclosed in Example I with the difference that 2.8 mols of ethylene oxide instead of 2.2 mols were used. 100 g. of this acid sulfate were neutralized with butylethanolamine while stirring, the amine being dropwise added to the surface of the acid sulfate the temperature being maintained at 30 C. After the equivalent amount of amine had been added the course of the neutralization reaction was followed in the way disclosed in Example I. It appeared that the total of 38.5 g. of butylethanolamine were required for the neutralization.
• C H OCH CH OSO OH wherein said C H radical is derived from lauryl alcohol and n is a number with an average value from 2 to .3, with diethylamine.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Animal Behavior & Ethology (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• Toxicology (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Dentistry (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Cosmetics (AREA)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

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Cited By (6)

Families Citing this family (1)

Citations (2)

• 0
  • NL NL91917D patent/NL91917C/xx active
  • NL NL219575D patent/NL219575A/xx unknown
• 1958
  • 1958-07-29 US US751645A patent/US3054820A/en not_active Expired - Lifetime
  • 1958-07-31 GB GB24724/58A patent/GB891631A/en not_active Expired

Patent Citations (2)

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