US3055834A - Anhydrous anion-active detergents in the form of aerosols - Google Patents

Anhydrous anion-active detergents in the form of aerosols Download PDF

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Publication number
US3055834A
US3055834A US738954A US73895458A US3055834A US 3055834 A US3055834 A US 3055834A US 738954 A US738954 A US 738954A US 73895458 A US73895458 A US 73895458A US 3055834 A US3055834 A US 3055834A
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US
United States
Prior art keywords
product
pressure
detergent
freon
anhydrous
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.)
Expired - Lifetime
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US738954A
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English (en)
Inventor
Charle Roger
Pomot Jean
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.)
LOreal SA
Monsavon LOreal SA
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LOreal SA
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Publication date
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Publication of US3055834A publication Critical patent/US3055834A/en
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0043For use with aerosol devices
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/31Anhydrous

Definitions

  • the projection of the mixture under the pressure of the gaseous propellant produces a foam consisting of a gaseous emulsion of the solvent in the aqueous surface-active solution of the detergent.
  • An additional subsidiary advantage resides in the gain in useful weight obtained, because the transportation of an undesirable quantity of water is avoided.
  • anion-active detergents commonly heretofore employed such as alkaline soaps, alkyl sulfates of alkaline metals, and the alkyl aryl sulfonates of alkaline metals
  • the liquefied gases ordinarily used as propellants which are usually of the type commercially known as Freons; methyl, ethyl or vinyl chlorides; butane, etc.
  • Freons methyl, ethyl or vinyl chlorides; butane, etc.
  • ammonium salts of these same anion-active substances are slightly soluble in the gaseous propellants mentioned at an ordinary temperature, although this solubility is completely insuflicient to obtain solutions which may be commercially utilized for the production of aerosols.
  • the object of the present invention is, first, to provide a new article of manufacture which comprises true solutions of certain anhydrous anion-active detergents in gases which have been liquefied under pressure. These solutions are intended to permit these detergents to be dispensed in the form of aerosols and are true solutions characterized by the fact that they are obtained by dissolving, in a liquefied propellant gas or mixture of gases selected from the following group:
  • R may be either (1) A saturated or unsaturated straight chain comprising from 8-22 carbon atoms and corresponding to fatty alcohols;
  • alkyl phenyl radical such as octylphenyl or nonylphenyl.
  • the number n of Formula I fall between 1 and 6. These values permit products to be obtained which have good detergent qualities, and a good solubility in the liquefied propellant gases.
  • the preferred value of it between these two extremes is a function of the nature of R in the general formula since, in general, a low value of n is conducive to starting the formation of the foam, to its abund; ance, and the detergent effect of the product obtained, whereas a high value of It improves the solubility of the sulfated product in the propellant.
  • the desired solubility may be obtained by using a mixtllre of slightly soluble products comprising, for example, one or two molecules of ethylene oxide in their molecules, with variable proportions of more soluble products comprising 5 or 6 molecules of ethylene oxide in their molecules.
  • a further object of the invention is to provide a method for directly preparing the anhydrous detergent solutions hereinbefore defined in the midst of the liquefied propellant gases.
  • products according to the general for may be obtained by reacting the sulfamic acid with oxyethylenated alcohols or alkylphenols, the reaction taking place at a temperature of about 125 to 135 C. by simple agitation of the solid sulfamic acid in the oxyethylene alcohol or in the oxyethylenated alkylphenol, the reaction taking place according to the following formula:
  • the object of the present invention is to prepare true solutions of anhydrous anion-active detergents in gases which have been liquefied under pressure, the process being characterized by the fact that the sulfamic acid is reacted with oxyethylenated alcohol or oxyethylenated alkylphenol in a solvent, this solvent having the following characteristics:
  • This solvent preferably comprises those boiling at a temperature sufficiently high that the reaction temperature, which is situated at about 120 C., may be attained without developing too high a pressure.
  • the process is carried out in an autoclave which is resistant to corrosion while agitating the reacting compositions at a temperature between 110 C. and 130 C. and under a pressure equal to the vapor tension of the solvent or mixture of solvents at that temperature.
  • urea in order to avoid the coloration which results from the traces of sulfuric acid contained in the sulfamic acid, and to facilitate the filtration of the solution at the end of the operation.
  • the quantity of urea used may run between 1 and by weight of the total of the alcohol and sulfamic acids used.
  • the constituant of the propellant mixture having the highest boiling point it is also preferable to select as a solvent the constituant of the propellant mixture having the highest boiling point, so as to operate at the lowest possible pressure.
  • the proportion of the solvent to the reaction mixture is dependent on the concentration of detergent which it is desired to obtain. It is always desirable to utilize to the utmost the capacity of the autoclave and to employ the minimum quantity of solvent required to obtain at the end of the reaction a solution sufliciently fluid when cold. For example, from 150 to 350 grams of solvent may be used per 100 grams of oxyethylenated alcohol or oxyethylenated alkylphenol, according to the degree of oxyethylenation. The weight of solvent required is the less as the degree of oxyethylenation is greater, since it is the degree of oxyethylenation which determines the solubility of the detergent in the solvent.
  • the mixture is cooled below the boiling point of the solvent at atmospheric pressure so that the overpressure in the autoclave is zero.
  • the residual acidity is neutralized either by introducing a measured quantity of gaseous ammonia into the autoclave or by adding a specific weight of an anhydrous amine, such as mono-, di-, or triethanolamine, so as to adjust the pH to a value of at least 7 and not more than 8.
  • an anhydrous amine such as mono-, di-, or triethanolamine
  • the solution is then discharged under pressure through a filter which removes those solid impurities which could block the expansion valves of the dispensing containers.
  • the solution obtained in this manner may be introduced directly into the dispensing containers.
  • the concentration and vapor pressure may be brought to the desired value by adding under pressure certain products known commercially as light Freons such as Freon 12" or a mixture of light Freons and other liquefied gases, such as butane.
  • Example 1 Into an autoclave made of stainless or enamelled steel, provided with an agitator and tested under a pressure of 30 kg./cm. the following ingredients are introduced:
  • the product is then filtered under pressure to separate out the urea and impurities.
  • the filtrate serves as the mother liquor A.
  • a true solution is thus obtained which contains 25% by weight of anhydrous detergent.
  • This solution may be perfumed as desired to provide a shampoo which may be sprayed onto the hair.
  • Example 11 The following ingredients are introduced into the autoclave described in connection with Example I:
  • the autoclave is brought to a temperature of C. while stirring, and kept at this temperature for about thirty minutes, with the pressure at about 13 kg./cm.
  • the autoclave is then cooled to 20 C. and the contents neutralized with a current of ammonia gas until a pH of 7.5 is obtained. Thecontents are then filtered under pressure to produce product B.
  • Example 111 Into an autoclave such as used to carry out the process of Example I, the following ingredients are introduced:
  • the temperature is brought to 125 C. while stirring and this temperature is maintained for 40 minutes, at a pressure of about 13 kg./cm.
  • the product prepared and treated in this manner provides, when sprayed, a very porous film of detergent, which may be used to wash windows and Windshields of automobiles.
  • Example IV Into an autoclave of the type used to carry out the processes of Example I and II the following ingredients are introduced:
  • a true solution is thus obtained which contains 32% of a detergent which, when sprayed, gives a finely divided aerosol'that produces a porous film on surfaces to be washed.
  • anhydrous solution of an anion-active detergent in a liquefied gas propellant such for example, as one or more of the products commercially known as Freons may be obtained.
  • This anhydrous solution is enclosed in a pressure-resistant metallic container provided with a valve for projecting the detergent in aerosol form onto objects to be washed.
  • Detergents which are thus applied in finely divided form have many uses, particularly for cosmetic purposes such as washing the skin and shampooing.
  • any suitable subsetnces such, for example, as fatty bodies, mineral oils, waxes, essences, perfumes, colorants, antiseptics, insecticides, etc., may be added to the solution.
  • An anhydrous detergent containing composition in a pressure container said composition being a true solution consisting essentially of:
  • At least one liquefied propellant gas selected from the group consisting of butane trichloromono-fluoromethane, dichlorodifluoromethane, and trichlorotrifluoroethane and their mixtures and (b) a detergent product having the formula in which R represents a radical selected from the group consisting of straight chains having not less than 8 nor more than 22 carbon atoms, corresponding to fatty alcohols; branch chains having not less than 10 nor more than 20 carbon atoms and corresponding toalcohols obtained by the 0x0 synthesis; octyl phenyl; and nonylphenyl; and n represents a number between 1 and 6, said liquified propellant gas being present in said combustion in major proportion, and said detergent product being present in said composition in minor proportion.
  • a detergent product having the formula in which R represents a radical selected from the group consisting of straight chains having not less than 8 nor more than 22 carbon atoms, corresponding to fatty alcohols; branch chains

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US738954A 1958-04-14 1958-06-02 Anhydrous anion-active detergents in the form of aerosols Expired - Lifetime US3055834A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR763106 1958-04-14

Publications (1)

Publication Number Publication Date
US3055834A true US3055834A (en) 1962-09-25

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Country Status (7)

Country Link
US (1) US3055834A (de)
BE (1) BE577602A (de)
CH (1) CH381247A (de)
DE (2) DE1118385B (de)
FR (1) FR1204531A (de)
GB (1) GB885008A (de)
NL (2) NL102547C (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277009A (en) * 1961-10-03 1966-10-04 Gen Aniline & Film Corp Water-soluble package and method for making and using same
US3384541A (en) * 1964-10-28 1968-05-21 William G. Clark Spermicidal vaginal pharmaceutical concentrate for producing nonaqueous foam with aerosol propellants
DE1298225B (de) * 1965-10-21 1969-06-26 Colgate Palmolive Co Textilbehandlungsmittel
US3866800A (en) * 1969-02-12 1975-02-18 Alberto Culver Co Non-pressurized package containing self-heating products
US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US4912337A (en) * 1988-06-03 1990-03-27 Honeywell Inc. Position responsive apparatus

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3395170A (en) * 1966-06-28 1968-07-30 Gen Aniline & Film Corp Sulfation of secondary alcohls

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE540036A (de) * 1955-04-12
GB485649A (en) * 1936-11-23 1938-05-23 Ig Farbenindustrie Ag Washing preparations
US2644831A (en) * 1951-04-16 1953-07-07 Monsanto Chemicals Alkali metal and ammonium sulfates of hydroxy ethers
US2655480A (en) * 1949-11-02 1953-10-13 Spitzer Lather producing composition
US2758977A (en) * 1951-05-25 1956-08-14 Gen Aniline & Film Corp Detergent composition and method of producing same
US2766212A (en) * 1952-09-16 1956-10-09 Gen Aniline & Film Corp Detergents

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB485649A (en) * 1936-11-23 1938-05-23 Ig Farbenindustrie Ag Washing preparations
US2655480A (en) * 1949-11-02 1953-10-13 Spitzer Lather producing composition
US2644831A (en) * 1951-04-16 1953-07-07 Monsanto Chemicals Alkali metal and ammonium sulfates of hydroxy ethers
US2758977A (en) * 1951-05-25 1956-08-14 Gen Aniline & Film Corp Detergent composition and method of producing same
US2766212A (en) * 1952-09-16 1956-10-09 Gen Aniline & Film Corp Detergents
BE540036A (de) * 1955-04-12

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277009A (en) * 1961-10-03 1966-10-04 Gen Aniline & Film Corp Water-soluble package and method for making and using same
US3384541A (en) * 1964-10-28 1968-05-21 William G. Clark Spermicidal vaginal pharmaceutical concentrate for producing nonaqueous foam with aerosol propellants
DE1298225B (de) * 1965-10-21 1969-06-26 Colgate Palmolive Co Textilbehandlungsmittel
US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US3866800A (en) * 1969-02-12 1975-02-18 Alberto Culver Co Non-pressurized package containing self-heating products
US4912337A (en) * 1988-06-03 1990-03-27 Honeywell Inc. Position responsive apparatus

Also Published As

Publication number Publication date
NL102547C (de) 1962-09-17
DE1201831B (de) 1965-09-30
FR1204531A (fr) 1960-01-26
DE1118385B (de) 1961-11-30
GB885008A (en) 1961-12-20
NL274124A (de) 1964-09-10
BE577602A (de) 1959-10-12
CH381247A (fr) 1964-08-31

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