US2743236A - Foaming compositions - Google Patents

Foaming compositions Download PDF

Info

Publication number
US2743236A
US2743236A US219504A US21950451A US2743236A US 2743236 A US2743236 A US 2743236A US 219504 A US219504 A US 219504A US 21950451 A US21950451 A US 21950451A US 2743236 A US2743236 A US 2743236A
Authority
US
United States
Prior art keywords
sulfone
detergent
carbon atoms
substituted
group
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
Application number
US219504A
Other languages
English (en)
Inventor
Rupert C Morris
Webster M Sawyer
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.)
Shell Development Co
Original Assignee
Shell Development Co
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
Priority to BE510389D priority Critical patent/BE510389A/xx
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US219504A priority patent/US2743236A/en
Priority to CH306349D priority patent/CH306349A/de
Priority to FR1057144D priority patent/FR1057144A/fr
Priority to GB8540/52A priority patent/GB717536A/en
Priority to DEN5322A priority patent/DE939347C/de
Application granted granted Critical
Publication of US2743236A publication Critical patent/US2743236A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/30—Organic compounds, e.g. vitamins containing nitrogen
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/32—Organic compounds, e.g. vitamins containing sulfur
    • 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
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3454—Organic compounds containing sulfur containing sulfone groups, e.g. vinyl sulfones

Definitions

  • This invention relates to the improvement of the foaming properties of solutions of surface-active agents, including Washing and cleaning agents and the like, and to new compositions having these improved properties.
  • albuminous materials derived from pro have been proposed to overcome the deficiency of these surface-active agents by the addition of various cornpounds.
  • teins, amine soaps of fatty acids and the like have been frequently suggested as desirable additives for fatty acid soaps in fire-fighting foam compositions, while higher alcohols, certain amides and fatty acid esters have been advanced as useful additives for synthetic detergents of certain types.
  • An important object is to provide advantageous combinations of surface-active compounds with more desirable additives which impart superior foaming properties to the new compositions of the invention.
  • a further object is the provision of detergent compositions of improved quality, and a special object is to provide washing and cleaning compositions based upon synthetic detergents which give a copious, long-lasting foam not obtainable with the detergent alone.
  • the foaming properties of surface-active agents in aqueous media can be materially improved by the addition of certain substituted sulfones.
  • These sulfone compounds are those having in the molecule a hydrophobic chain containing about 8 to 18 carbon atoms and an imido carbonyl group I II to which is attached, through not more than 4 intervening carbon atoms, a sulfone group directly linked to 2 carbon atoms.
  • the R in the indicated imido carbonyl group may be a hydrogen atom or a hydrocarbon radical.
  • the sulfone compound used may contain more than one imido, carbonyl and sulfone groups in the molecule but it is essential that at least one sulfone group of the type be present in combination with an imido carbonyl group as above described in order to obtain the advantages of the invention.
  • R and R represent hydrogen or a hydrocarbon radical
  • R represents a hydrocarbon radical
  • R represents a hydrocarbon radical linking the sulfone group --SO2 to the carbonyl carbon atom by a chain of not more than 4 carbon atoms
  • n is an integer which may be zero or one.
  • At least one of the radicals R and R is a hydrocarbon radical containing a chain of 8 to 18 carbon atoms, most preferably a straight or only slightly branched chain of 10 to 16 carbon atoms.
  • Preferred compounds of this type are saturated amides of sulfonesubstituted carboxylic acids.
  • One suitable method of preparing sulfone compounds of this type is by oxidation with nitric acid, for example, of the corresponding thioether-substituted carboxylic acids, which may be conveniently formed by addition of a mercaptan to an unsaturated carboxylic acid, and reaction of the sulfone-substituted carboxylic acid produced by the oxidation with a suitable amine.
  • a typical synthesis of this type is the preparation of N-myristyl beta- (methyl sulfonyl)propionamide from acrylic acid, methyl mercaptan and lauryl amine in accordance with the following equations
  • the first step in this synthesis namely, adding a mercaptan to the starting olefinic compound, can be carried out in accordance with the methods of the following references to this type of reaction: Annual Reports of the Chemical Society (London), 1905, page J. Am. Chem. Soc., vol. 60, pages 2452 and 2731 (1938), and vol. 61, page 70 (1939).
  • the second step of oxidizing the sulfide to sulfone is a reaction described, for example, in J. Am. Chem.
  • V represents a divalent'hydrocarbon radical directly connected to R or those whereincR represents a divalent group are, for instance: a V
  • the second important type of sulfone-substituted compounds which has been found to beespecially effective in :increasing the volume and stability of the foam of aqueous solutions of surface-active compounds is that comprising the amides of sulfone-substituted amines which may be represented by the general formula:
  • R and R represent hydrocarbon radicals
  • the preferred sulfone-substituted compounds are saturated sulfone subStituted amides having a total of 11 to about 30 carbon atomsper molecule.
  • Sulfone s'ubstituted amines which maybe usedas starting materials-for the preparation of useful additives in' accordance with the invention are'readily produced,for example, from olefinic amines by addition of a mercaptan andoxidation of the sulfide sulfur atoms iof'grejsulting, product.
  • Typical amides of sulfone-substituted amines which are advantageous inimproving foaming properties in aecordancewith the invention are, foroinstance: 'j
  • U. S. Patent 2,435,071 discloses and claims one type of sulfone compounds of this class which is eminently suitable provided a hydrocarbon radical, preferably an alkyl radical, of 8 to 18, most preferably 10 to 16, carbon atoms is present in the molecule.
  • N- (2-sulfolany1) myristamide CH3(CH2)1ICHCH-NH-l-CH: (1H2 (IJHQ N-(3-dodecy1-4-sulfolanyl) acetamide are typical of these preferred additives.
  • other cyclic sulfone amides such as o /QHr-CH2 H CHNHC--(CH2)HCH3 '0? om-o i N-(4-thianyl- 1-dioxide) palmitamide etc. are. also useful as additives for surface-active comhas'been'emphasized in the foregoing, it will be understood that mixtures of two or more such compounds are equally useful.
  • a sulfone-substituted amine may be reacted with a mixture of suitable carboxylic acids, for instance, the mixed acids derived from animal or vegetable oils, fats or waxes, or a mixture of sulfone-substituted amines may be similarly. reacted with one or more carboxylic acids to obtain a mixture of sulfone-substituted amides which are useful in the invention.
  • a single amine or a mixture of such amines may be amidified with a plurality of sulfone-substituted carboxylic acids to obtain a mixture of sulfone-substituted amides which are effective foam-improving agents.
  • the amides of sulfone-substituted amines and sulfone-substituted carboxylic acids are useful additives for use in the invention. Suitable compounds of this type are, for instance:
  • the amount of sulfone-substituted amide which it will be desirable to use in a given case will depend upon the particular sulfone-substituted amide or mixture of such amides which is chosen, the surface-active agent with which it is to be used and the intended use to which the mixture is to be applied. However, as a general rule, amounts between about 1% and 50% by weight of the surface-active agent present are suitable, and amounts between about 5% and about 30% are often most advantageous.
  • the sulfone-substituted amides are effective in improving the foaming properties of a wide variety of surface-active salts of organic acids.
  • the generally used surface-active organic acid salts are watersoluble salts of carboxylic, sulfonic, phosphoric and like acids and of sulfonic acid esters having a hydrocarbon chain of at least 8 carbon atoms in the molecule. Mixtures of two or more of these surface-active organic acid salts of the same or of different types may be used in the new compositions.
  • Preferred organic acid salts are the alkali metal, e. g. sodium and potassium, or ammonium or amine, particularly the alkylolamine, salts.
  • Synthetic detergents are the especially preferred type of soap used in the new compositions because of the outstanding improvement obtained by the addition of the described sulfone-substituted amides to these compounds.
  • the sulfonates i. e. the salts of organic acids having a 4O3H group which may be linked directly, or through an oxygen atom as in the sulfuric acid esters, to a hydrophilic group, are the preferred sub-group of synthetic detergents used in the invention.
  • the salts of organic sulfonic acids which can be improved substantially in foaming properties are the salts of alkyl aryl sulfonic acids.
  • sulfonates of this type which have been successfully used are salts, particularly the alkali metal salts, of sulfonic acids such as are obtained by alkylating an aromatic hydrocarbon of the benzene series, particularly benzene or toluene, with an alkylating agent having preferably 8 to 16 carbon atoms per molecule such as an olefin, an olefin polymer or an alkyl halide, and converting the alkyl aromatic hydrocarbon thus formed into the corresponding monosulfonic acid which is'then neutralized.
  • an alkylating agent having preferably 8 to 16 carbon atoms per molecule
  • alkyl aryl sulfonate salts which can ire-used, as can the .keryl benzene, toluene, etc., sulfonates 'described:in U.-S. Patent 2,340,654, for instance.
  • Y carbon atoms as Ethe hydrophobic group :of the detergent -of .alkyl aryl-sulfonate salts
  • 'alkyl sulfonic acid salts such as-are obtainable by the methods of U. S. Patents 2,263,312 .and 2,276,090,for example, areoperative in the new compositions of :the invention.
  • alkyl sulfuric acid esters of 8 to 18 carbon atoms obtained from predominantly normal, terminally unsaturated mono-olefins such as can be obtained by cracking parafiin wax as described in U. S. Patent 2,152,297.
  • alkyl, .”sulfonic acidisalts are the 2-alkyl sodium sulfonates hav preferably; amides having ahydrophobicchain of about t -carbon atoms less'toabout number of are. used. Where mixtures of.detcrgents .and/ or additives are being used, .the average chain lengths ould pr'ofera ably. have this relation toieach other.
  • stituted amide' may.be .mechanically mixed into thedry detergent or into a slurry thereof, oritmay he added to an aqueous solution of the sulfonic acid or acid sulfate before the neutralization-step in the process of produc ing detergents of these typcs.-'---
  • the alkali metal salts of sulfuric acid esters of normal primary aliphatic alcohols such as may be obtained by hydrogenation of fatty oils i such, for instance, .as coconut, babassu, palm kernel, etc.,
  • hydrocarbon sulfonate salts such as described above are a preferred type of synthetic detergent for use in the new compositions
  • improvement in foaming properties can also be obtained with-substituted hydrocarbon sulfonat e salts containing, for example, halogen, ether oxygengcarbonylcarboxyl, and like atoms or groups.
  • water-soluble salts of sulfuric acid esters of hydroxy ethers of higher molecular alcohols such as the sodium sulfates of monoor' di-ethylene glycol mono-myristyl ether, or
  • glycerinemonolaurate monosodium sulfate and-ethylene glycol monostearate monosodium sulfate are examples, are included amongthe sulfonate saltdetergents which are benefitedfby the addition of a sulfonesubstituted amide.
  • Corresponding detergents having a true'sulfonic acid group in place of the sulfuric acid groupv of the foregoing compounds are likewise improved in foaming properties.
  • salts of sulfoacetic acid esters and-alcohols Of-S to 20 carbon atoms and salts of higher fatty acids with hydroxy sulfonic acids such as -isethionicjaoid, and salts of amides of amino sulfonic -acids,-such as'N-methyl taurine, with higher fattyacids This is also true of the water-soluble
  • the following examples illustrate some typical appli cations of the inventionand show some-of its advantages.
  • Foam tests were carried out with N-(3-sulfolanyl) lauramide; as additive in a number of synthetic detergents of difierent types'built with sodium'tripolyphosphate and sodium sulfate so that the active detergentiingredient content was 1 8% by weight. seconds shaking in a mechanical shaking machine which insured reproducible results and in the presence of standard soil cloth.
  • Dodecyl benzene magnesiu'm sulfonate 18 NasPaOio 24 Na4PaO'z l 24 -N-(3-sulfolanyl) lauramide :0 ms MgSO4 and NazSO4 Remainder h f0 l ins e u r typi ai rd tetsqn la o u m Similar good results are obtained when N-. (3-sulfolanyl) myristamide, N-(Z-methylsulfonyl ethyl) capramide, N- (2-dodecylsulfonyl ethyl) acetamide, beta:
  • amides which do not contain a sulfonic group linked to the imido carbonyl group by a chain of not more than 4 carbon atoms are used.
  • examples of such amides are, for instance, caprylamide, dimethyl lauramide, lauramide, stearamide, lauryl lauramide, butyl capramide, dibutyl myristamide and N-lauroyl' morpholine which, when added to the foregoing synthetic deter-- gents under the same conditions, produce little or no improvement in the final foam volume or the foam stability.
  • the sulfone-substituted amide additives of the invention produce their remarkable improvement in foam prop- I erties without any undesirable effects upon the other ad- Relative Detergeney at a. lgetergent Concentration Without additive 18. 5 52. 5 57. 5 With 4% of additive 31. 6 55. 0 60.0
  • the invention oifers many advantages and is capable of wide application not only in respect to the detergents which can be employed and the sulfone-substituted amides which can be used therewith, but also in regard to the method of application of the new compositions.
  • the new compositions are not only effective alone but can be used advantageously in combination with other materials.
  • Any of the usual soap additives, including bleaching agents, perfumes, dyes, builders such as trisodium phosphate, tetrasodium pyrophosphate, sodium carbonate, sodium silicate, carboxymethyl cellulose, etc., may be included, as may any of the customary materials used in preparing emulsions and the like. It will therefore be understood that the invention is not restricted to the compositions given by way 10 of illustration nor by any theory proposed in explanation of the improved results which are obtained.
  • a surface-active composition having improved foaming properties in aqueous solution which comprises anionic detergent of the group consisting of water-soluble fatty acid soap and water-soluble synthetic organic sulfonated and sulfated detergents, together with about 1% to about 50% by weight of the detergent of sulfonesubstituted carboxylic acid amide having the sulfone group linked to the imido carbonyl group no III wherein R is a member of the group consisting of the hydrogen atom and hydrocarbon radicals having not more than 18 carbon atoms) by a chain of not more than 4 carbon atoms and containing a saturated aliphatic hydrocarbon radical having 8 to 18 carbon atoms.
  • a surface-active composition which comprises an anionic detergent of the group consisting of the watersoluble fatty acid soap and water-soluble synthetic organic sulfonated and sulfated detergents, together with about 1% to about 50% by weight of the detergent of N- (sulfolanyl) lauramide.
  • a detergent comprising an intimate mixture of at least one anionic water-soluble surface-active synthetic organic sulfonated salt detergent, together with 1% to 50% -by weight of said surface-active salt detergent of saturated aliphatic carboxylic acid amide having a sulfone group linked to an imido carbonyl group R0 Ill wherein R is a member of the group consisting of the hydrogen atom and hydrocarbon radicals having not more than 18 carbon atoms) by a hydrocarbon chain of not more than 4 carbon atoms and an aliphatic hydrocarbon radical of 8 to 18 carbon atoms which is not longer than the hydrophobic group of said synthetic organic sulfonated salt detergent.
  • a detergent comprising a mixture of at least one anionic water-soluble sulfonate salt detergent, together with about 5% to 30% by weight of said sulfonate salt detergent of a N-(sulfolanyl) amide ot' a saturated carboxylic acid having 10 to 16 carbon atoms per molecule.
  • a detergent comprising an intimate mixture of at least one anionic water-soluble alkyl aryl sulfonic salt detergent having an alkyl group of 10 to 16 carbon atoms, together with about 1% to about 50% by weight of said anionic water-soluble salt of a substituted sulfone having in the molecule a saturated aliphatic hydrocarbon chain containing 8 to 18 carbon atoms and an imido carbonyl group wherein R represents a member of the group consisting of the hydrogen atom and hydrocarbon radicals having not more than 18 carbon atoms) to which is attached through not more than four intervening carbon atoms a sulfone group directly linked to two carbon atoms.
  • a detergent in accordance with claim 6 wherein the sulfone-substituted amide is an amide of a sulfone-substituted saturated carboxylic acid.
  • a detergent comprising an intimate mixture of at least one anionic water-soluble salt of an alkyl aryl sulfonic acid having an alkyl group of 10 to 16 carbon atoms, together with about 1% to about 50% by weight of said sulfonate of an amide of a higher fatty acid containing a hydrocarbon radical of 8 to 18 carbon atoms and an being linked to the imido carbonylgroup wherein R represents a member of the group consisting of the hydrogen atom and hydrocarcon radicals having not more than 18 carbon atoms) to which is attached through not more than four intervening carbon atoms a sulfone group directly linked to two carbon atoms.
  • a surface-active Composition which comprises an anionic water-soluble, surface-active alkyl aryl sulfonate salt detergent, together with'about 1% to about 50% by weight of the detergent of anN-(sulfolanyl) amide of a saturated carboxylic acid, which acid contains 10't0 16 carbon atoms per molecule.

Landscapes

  • 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)
US219504A 1951-04-05 1951-04-05 Foaming compositions Expired - Lifetime US2743236A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE510389D BE510389A (en, 2012) 1951-04-05
US219504A US2743236A (en) 1951-04-05 1951-04-05 Foaming compositions
CH306349D CH306349A (de) 1951-04-05 1952-04-03 Oberflächenaktives Gemisch mit verbessertem Schaumbildungsvermögen.
FR1057144D FR1057144A (fr) 1951-04-05 1952-04-03 Compositions tensio-actives possédant d'excellentes propriétés moussantes
GB8540/52A GB717536A (en) 1951-04-05 1952-04-03 Improvements in or relating to foam-producing compositions
DEN5322A DE939347C (de) 1951-04-05 1952-04-04 Oberflaechenaktive Gemische mit verbessertem Schaumbildungsvermoegen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US219504A US2743236A (en) 1951-04-05 1951-04-05 Foaming compositions

Publications (1)

Publication Number Publication Date
US2743236A true US2743236A (en) 1956-04-24

Family

ID=22819537

Family Applications (1)

Application Number Title Priority Date Filing Date
US219504A Expired - Lifetime US2743236A (en) 1951-04-05 1951-04-05 Foaming compositions

Country Status (6)

Country Link
US (1) US2743236A (en, 2012)
BE (1) BE510389A (en, 2012)
CH (1) CH306349A (en, 2012)
DE (1) DE939347C (en, 2012)
FR (1) FR1057144A (en, 2012)
GB (1) GB717536A (en, 2012)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4260497A (en) * 1979-11-26 1981-04-07 Colgate-Palmolive Company Methanesulfonamides as antistatic agents for laundered fabrics
US4317779A (en) * 1980-08-21 1982-03-02 The Procter & Gamble Company Alpha-sulfoxide and alpha-sulfone carboxyl compounds
US4395363A (en) * 1980-08-21 1983-07-26 The Procter & Gamble Company Alpha-sulfoxide and alpha-sulfone carboxyl compounds
CN108291055A (zh) * 2015-11-12 2018-07-17 诺华丝国际股份有限公司 作为溶剂的含硫化合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1932180A (en) * 1929-04-12 1933-10-24 Ig Farbenindustrie Ag Sulphuric acid derivatives of amides
US2432850A (en) * 1941-05-02 1947-12-16 Chem Ind Basel Water-soluble condensation products and process of making same

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR873351A (fr) * 1940-07-24 1942-07-07 Deutsche Hydrierwerke Ag Succédanés de savon
US2383737A (en) * 1942-02-18 1945-08-28 Procter & Gamble Detergent composition
US2383525A (en) * 1942-02-19 1945-08-28 Procter & Gamble Detergent composition
US2383738A (en) * 1942-02-20 1945-08-28 Procter & Gamble Detergent composition
US2383739A (en) * 1942-07-02 1945-08-28 Procter & Gamble Detergent composition
US2383740A (en) * 1943-12-06 1945-08-28 Procter & Gamble Detergent composition
US2527076A (en) * 1947-02-24 1950-10-24 Procter & Gamble Detergent composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1932180A (en) * 1929-04-12 1933-10-24 Ig Farbenindustrie Ag Sulphuric acid derivatives of amides
US2432850A (en) * 1941-05-02 1947-12-16 Chem Ind Basel Water-soluble condensation products and process of making same

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4260497A (en) * 1979-11-26 1981-04-07 Colgate-Palmolive Company Methanesulfonamides as antistatic agents for laundered fabrics
US4317779A (en) * 1980-08-21 1982-03-02 The Procter & Gamble Company Alpha-sulfoxide and alpha-sulfone carboxyl compounds
US4395363A (en) * 1980-08-21 1983-07-26 The Procter & Gamble Company Alpha-sulfoxide and alpha-sulfone carboxyl compounds
CN108291055A (zh) * 2015-11-12 2018-07-17 诺华丝国际股份有限公司 作为溶剂的含硫化合物
EP3374428A4 (en) * 2015-11-12 2019-06-05 Novus International Inc. SULFUR COMPOUNDS AS SOLVENTS
CN108291055B (zh) * 2015-11-12 2021-07-06 诺华丝国际股份有限公司 作为溶剂的含硫化合物

Also Published As

Publication number Publication date
CH306349A (de) 1955-04-15
BE510389A (en, 2012)
DE939347C (de) 1956-02-23
GB717536A (en) 1954-10-27
FR1057144A (fr) 1954-03-05

Similar Documents

Publication Publication Date Title
USRE23840E (en) Liquid anionic-dialkylolamide
US2619467A (en) Detergent mixtures containing
US2679482A (en) Synthetic detergent compositions
US2527076A (en) Detergent composition
US2329086A (en) Sulphonated amides and process of producing same
US2743236A (en) Foaming compositions
US3954660A (en) Anionic surfactant slurry having increased viscosity and method of providing said slurry
US3705113A (en) Hydrogenated olefin sulfonate-alkyl-1,2-glycol detergent compositions
US3029264A (en) Preparation of a mixture of fattyacyl-oxyalkane sulphonates
JPH05507473A (ja) グリセリンエーテルスルフェートの製造方法
US2806044A (en) Esters of hydroxyalkanesulfonates with alpha-sulfonated long-chain fatty acids
US2662898A (en) Alkanol-ether-imides of long-chain aliphatic dicarboxylic compounds
JPS609557B2 (ja) 新規な液体洗浄剤組成物
US2738333A (en) Surface-active compounds and detergent compositions containing same
US3527707A (en) Liquid detergent composition
US2868812A (en) Manufacture of fatty acid monoesters of glycerol monosulfuric acid and salts thereof
US2326270A (en) Chemical compound and process
US2427577A (en) Production of ether sulphonates
US3345301A (en) Pourable and free-flowing detergent, wetting, and emulsifying compositions
US2156996A (en) Detergent and wetting compositions
US3867317A (en) Synthetic detergent bars containing calcium olefin sulfonates
US3776861A (en) Dry powder bubblebath composition
US2708183A (en) Long-chain urea compounds in detergent compositions
US3005777A (en) Manufacture of surface-active compositions
US2373863A (en) Nonalkaline detergent composition