US2766212A - Detergents - Google Patents

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Publication number
US2766212A
US2766212A US309953A US30995352A US2766212A US 2766212 A US2766212 A US 2766212A US 309953 A US309953 A US 309953A US 30995352 A US30995352 A US 30995352A US 2766212 A US2766212 A US 2766212A
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US
United States
Prior art keywords
salt
moles
weight
group
water soluble
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
US309953A
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English (en)
Inventor
Richard A Grifo
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 BE522826D priority Critical patent/BE522826A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US309953A priority patent/US2766212A/en
Priority to GB22900/53A priority patent/GB738538A/en
Priority to FR1083752D priority patent/FR1083752A/fr
Priority to DEG12629A priority patent/DE1013379B/de
Application granted granted Critical
Publication of US2766212A publication Critical patent/US2766212A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • Y10S516/02—Organic and inorganic agents containing, except water

Definitions

  • This invention relates to detergent compositions, and more particularly to detergent compositions of the polyoxy-alkylene type, and processes for employing same.
  • a detergent composition comprising a water soluble salt of a polyvalent metal and a compound of the formula in which R is a hydrocarbon radical containing at least carbon atoms selected from the group consisting of alkyl radicals containing a plurality of branched chains, and alkylaryl radicals, X is selected from the group consisting of H and CH3, M is a monovalent water solubilizing cation, and n is from 1 to 8.
  • compositions of this invention have been found to have improved foaming and foam-stable properties in addition to increased rates of detergency and detergent efficiencies with respect to compositions containing the same polyoxyalkylene compounds but without the polyvalent metal salts.
  • the mechanism whereby the improved results are obtained is not thoroughly understood, but it is apparent that some synergistic effect is involved. This should be apparent from the fact that the water soluble salts of polyvalent metals do not per se have any foaming or detergent properties. It is, therefore, indeed surprising that the addition of these water soluble salts of polyvalent metals to polyoxyalkylene compounds of the abovementioned type improves the foaming and detergent properties of such compounds to the remarkable extent described herein.
  • such compounds may be derived from branched chain primary aliphatic alcohols such as: 2,4,S,5,7-pentamethyl-l-octanol, 2,3,5,7-tetramethyll-nonanol, 3,5-diethyl-l-octanol, 2,4,7-trimethyl-1-nonanol, 2,4,5,6,8-pentamethyl-l-nonanol, 2,6,7-trimethyl-3- ethyl-l-octa-nol, 2,4,6,8-tetramethyl-l-nonanol, 2,3,5-trimethyl-4,7-diethyll-octanol, 2,3,5,6 tetramethyl-5,7-diethyl-l-octanol, 3,5-dimethyl-4,6-diethyl-l-heptanol, 3,4,5- trimethyl-4,6-diethyl-l-heptanol, 2-ethyl-3,5,
  • alcohols may be used which are prepared by the catalytic reaction of an olefin such as tripropylene, tetrapropylene, penta- States atent O ice propylene, triisobutylene, tetraisobutylene, tributene, 4,6,8-trimethyl-l-nonene, 4,6,8-trimethyl-2-nonene, mixed propene-butene polymers, 5,7,7-trimethyl-l-octene, 3,5,7- trimethyl-l-heptene, and 2,4,6,6,8-pentamethyl-l-nonene, with carbon monoxide and hydrogen to form an aldehyde followed by catalytic reduction of this aldehyde to an alcohol.
  • an olefin such as tripropylene, tetrapropylene, penta- States atent O ice propylene, triisobutylene, tetraisobutylene, tributene, 4,6,8-trimethyl-
  • This two-stage process is known as the oxo process.
  • Alcohols produced by the 0x0 process may be designated as oxo alcohols.
  • the 0x0 tridecyl alcohol mentioned hereinafter and in the claims is the C13H27OH polybranched chain primary aliphatic alcohol prepared from tetrapropylene by the 0x0 process.
  • Such compounds may be derived from alkylated aromatic hydroxy compounds such as p-n butylphenol, amycresol, diisobutylphenol, diamylphenol, isohexylnaphthol, oleylphenol, isododecylphenol, isooctylresorcin01, nonylphenol, dinonylphenol, isoootylphenol, isooctyl-fi-naphthol, isohexylxylenol, n-octadecylphenol, and the like.
  • alkylated aromatic hydroxy compounds such as p-n butylphenol, amycresol, diisobutylphenol, diamylphenol, isohexylnaphthol, oleylphenol, isododecylphenol, isooctylresorcin01, nonylphenol, dinonylphenol, isooo
  • the invention is particularly effective when employing v the ammonium, sodium, potassium, alkylammonium or hydroxyalkylammonium, salts of the sulfuric acid esters of polyoxyalkylene compounds of the above-mentioned type containing from about 1 to 8, and preferably 1 to 6 polyoxyalkylene groups.
  • Compounds containing 24 polyoxyalkylene groups are particularly preferred. Outstanding results are obtained when the compound is derived from oxotridecyl alcohol and ethylene oxide.
  • the water soluble salts of polyvalent metals which may be employed are, for example, the chlorides, sulphates, nitrates, bromides and acetates of magnesium, calcium, aluminum and iron or mixtures thereof. In some cases, it is preferable to use the hydrates of the aforementioned salts. Because of the required water solubility and other characteristics, the magnesium and calcium chlorides are preferred. These salts or mixtures thereof are employed in proportions of about 5 to 50% .and preferably from about 10 to 45% by weight of the polyoxyalkylene compound.
  • composition of this invention When employed for detergent purposes, relatively small amounts of the composition of this invention are required to be dissolved in aqueous solution.
  • a solution containing .05 of the active polyoxyalkylene compound is suflicient to provide improved detergent and foam producing properties, although larger or smaller amounts may be employed when desired.
  • the optimum amount in any particular instance will, of course, be readily determinable by a worker skilled in the art.
  • Concentrates may be prepared for market in liquid or powdered form, or the like.
  • the outstanding properties of the composi tions of this invention are especially noticeable when employed in deionized, distilled or very soft water. 7 V
  • the hand dishwashing test consists essentially of washing dishes of 9" diameter, spread with 3 g. of a melted mixture of 80 parts Crisco, ZO'parts ordinary bread flour, and 0.5 parts Oildag ⁇ graphite in oil). The number of dishes washed before the foam disappears is considered to be the end point for this test.
  • the time required to wash 8 dishes is also an imaprtant- TABLE 1 Hand dishwashing test No. of Time to Product (0.05-lactive material in Soilcd Wash 8 Example distilled water) Dishes Dishes To Breakl ljMin.)
  • composition consisting essentially of a compound of the formula:
  • R is a hydrocarbon radical containing from about 10 to 24 carbon atoms selected from the group consisting of alkyl radicals containing a plurality of branched chains, and alkylaryl radicals
  • X is selected from the group consisting of H and CH3
  • M is a monovalent water-solubilizing cation
  • n is from 1 to 8, and about 5 to 50% by weight thereof of a water soluble salt of a polyvalent metal wherein said metal is selected from the group consisting of magnesium, calcium, iron and aluminum.
  • composition consisting essentially of a compound of the formula:
  • R is a hydrocarbon radical containing from about 10 to 24 carbon atoms selected from the group consisting of alkyl radicals containing a plurality of branched chains, and alkylaryl radicals
  • X is selected from the group consisting of H and CH3
  • M is a monovending water-solubilizing cation
  • n is from 1 to 8
  • composition consisting essentially of a compound of the formula:
  • R is a hydrocarbon radical containing from about 10 to 24 carbon atoms selected from the group consisting of alkyl radicals containing a plurality of branched chains, and alkylaryl radicals
  • X is selected from the group consisting of H and CH3
  • M is a monovalent water-solubilizing cation
  • n is from 1 to 8, and about 5 to 50% by weight thereof of a mixture of magnesium chloride and calcium chloride.
  • a composition consisting essentially ofabout by weight of the ammonium salt of the sulfuric acid ester of the condensation product of one mole of oxotridecyl alcohol with two moles of ethylene oxide and about 20% by weight of magnesium chloride.
  • a composition consisting essentially of about 70%. by weight of the ammonium salt of the sulfuric acid ester of the condensation product of one mole of oxotridecyl alcohol with two moles of ethylene oxide, about 12%, by weight of magnesium chloride and about 18% by weigh of calcium chloride.
  • a composition consisting essentially of about 70% by weight of the sodium salt of the sulfuric acid ester of the condensation product of one mole of isooctylphenol with four moles of ethylene oxide, about 12% by weight of magnesium chloride and about 18% by weight of calcium chloride.
  • a composition consisting essentially of about 70% by weight of the ammonium salt of the sulfuric acid ester of the condensation product of one mole of nonylphenol with four moles of ethylene oxide, about 12% by weight of magnesium chloride and about 18% by weight of calcium chloride.
  • composition consisting essentially of about 80% by weight of the ammonium salt of the sulfuric acid ester of the condensation product of one mole of nonylphenol of magnesium chloride.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of a condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of a primary aliphatic alcohol of about to 20 carbon atoms containing a plurality of branched chains, and about 5 to 50% by weight thereof, of a water soluble salt of a polyvalent metal wherein said metal is selected from the group consisting of magnesium, calcium, iron and aluminum.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of a condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of a primary aliphatic alcohol of about 10 to 20 carbon atoms containing a plurality of branched chains, and about 10 to 45% by weight thereof of magnesium chloride.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of a condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of a phenol substituted by an alkyl group of at least four carbon atoms, and about 5 to 50% by weight thereof of a water soluble salt of a polyvalent metal wherein said metal is selected from the group consisting of magnesium, calcium, iron and aluminum.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of a condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of a phenol substituted by an alkyl group of at least four carbon atoms, and about 5 to 50% by weight thereof of magnesium chloride.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of the condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of isooctylphenol and about 5 to 50% by weight thereof of a water soluble salt of a polyvalent metal wherein said metal is selected from the group consisting of magnesium, calcium, iron and aluminum.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of the condensation product of about 1 to 8 moles of ethylene by weight thereof of a water soluble salt of a polyvalent metal wherein said metal is selected from the group consisting of magnesium, calcium, iron and aluminum.
  • a composition consisting essentially of a monovalent water soluble salt of the sulfuric acid ester of the condensation product of about 1 to 8 moles of ethylene oxide with 1 mole of nonylphenol and about 5 to by weight thereof of magnesium chloride.
  • a washing process comprising contacting soiled objects with a composition consisting essentially of a compound of the formula:
  • R is a hydrocarbon radical containing from about 10 to 24 carbon atoms selected from the group consisting of alkyl radicals containing a plurality of branched chains, and alkylaryl radicals
  • X is selected from the group consisting of H and CH3
  • M is a monovalent water-solubilizing cation
  • n is from 1 to 8 and about 5 to 50% by weight thereof of a water-soluble salt of a polyvalent metal, said metal selected from the group consisting of magnesium, calcium, iron and aluminum.
  • composition as defined in claim 1 wherein said salt is selected from the group consisting of the sulfates, chlorides, bromides, nitrates and acetates of said polyvalent metal.
  • said salt is selected from the group consisting of the sulfates, chlorides, bromides, nitrates and acetates of said polyvalent metal.
  • composition as defined in claim 9 wherein said alcohol is oxotridecyl alcohol.

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US309953A 1952-09-16 1952-09-16 Detergents Expired - Lifetime US2766212A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE522826D BE522826A (fr) 1952-09-16
US309953A US2766212A (en) 1952-09-16 1952-09-16 Detergents
GB22900/53A GB738538A (en) 1952-09-16 1953-08-19 Detergent compositions
FR1083752D FR1083752A (fr) 1952-09-16 1953-08-24 Détersifs
DEG12629A DE1013379B (de) 1952-09-16 1953-09-11 Reinigungsmittel

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US309953A US2766212A (en) 1952-09-16 1952-09-16 Detergents

Publications (1)

Publication Number Publication Date
US2766212A true US2766212A (en) 1956-10-09

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US309953A Expired - Lifetime US2766212A (en) 1952-09-16 1952-09-16 Detergents

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US (1) US2766212A (fr)
BE (1) BE522826A (fr)
DE (1) DE1013379B (fr)
FR (1) FR1083752A (fr)
GB (1) GB738538A (fr)

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2908651A (en) * 1954-05-07 1959-10-13 Colgate Palmolive Co Liquid detergent composition
US2956947A (en) * 1957-08-06 1960-10-18 Union Carbide Corp Fire extinguishing method
US2970963A (en) * 1958-04-23 1961-02-07 Procter & Gamble Opaque liquid detergent composition
US3055834A (en) * 1958-04-14 1962-09-25 Oreal Anhydrous anion-active detergents in the form of aerosols
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3223186A (en) * 1962-05-23 1965-12-14 Pan American Corp Method of drilling with air or gas
US3229777A (en) * 1961-03-22 1966-01-18 Swift & Co Method of transporting water from a well as a substantially stable foam
US3320172A (en) * 1964-12-07 1967-05-16 Domtar Ltd Detergent composition
US3391750A (en) * 1965-08-09 1968-07-09 Union Carbide Corp Surfactant composition
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3852030A (en) * 1970-03-19 1974-12-03 Gaf Corp Surfactant for electrolyte-containing processing solutions
JPS502003A (fr) * 1973-05-08 1975-01-10
JPS5013403A (fr) * 1973-06-08 1975-02-12
US3898186A (en) * 1973-04-09 1975-08-05 Procter & Gamble Dishwashing compositions containing gel forming gelatin
US3910978A (en) * 1973-05-31 1975-10-07 Alcolac Inc Aqueous soluble mixed complex salts of aluminum aliphatic alcohol sulfates
US3919125A (en) * 1972-05-23 1975-11-11 Nippon Unitol Co Ltd Method of preparing a highly concentrated solution of a higher secondary alcohol ethoxysulfate and such a concentrated solution
US3954649A (en) * 1974-09-16 1976-05-04 Lever Brothers Company Detergent compositions containing coated particulate calcium sulfate dihydrate
JPS51125405A (en) * 1975-01-06 1976-11-01 Procter & Gamble Semiipolar nonionic detergent and detergent composition containing alkali earth metal anion
US3997692A (en) * 1974-09-16 1976-12-14 Lever Brothers Company Process of coating calcium sulfate dihydrate detergent filler particles
US3998750A (en) * 1975-06-30 1976-12-21 The Procter & Gamble Company Liquid detergent composition
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4054541A (en) * 1974-11-04 1977-10-18 Witco Chemical Corporation Spray dried alcohol ether sulfate detergent compositions
US4075129A (en) * 1975-03-20 1978-02-21 Kao Soap Co., Ltd. Detergent composition
US4129515A (en) * 1976-09-13 1978-12-12 The Procter & Gamble Company Heavy-duty liquid detergent and process
US4132680A (en) * 1976-06-24 1979-01-02 The Procter & Gamble Company Detergent compositions having soil release properties
US4166048A (en) * 1975-09-22 1979-08-28 Kao Soap Co., Ltd. High foaming detergent composition having low skin irritation properties
US4174291A (en) * 1972-04-28 1979-11-13 The Procter & Gamble Company Crystallization seed-containing composition
US4188311A (en) * 1975-07-24 1980-02-12 Chem-Y, Fabriek Van Chemische Produkten B.V. Detergent compositions containing ether sulfates
US4299739A (en) * 1976-03-25 1981-11-10 Lever Brothers Company Use of aluminum salts in laundry detergent formulations
US4524002A (en) * 1983-02-23 1985-06-18 Gaf Corporation Foaming agent
US4699623A (en) * 1984-11-21 1987-10-13 Atochem Process of bleaching laundry
US4923635A (en) * 1987-07-06 1990-05-08 Colgate-Palmolive Company Liquid detergent composition containing alkylbenzene sulfonate, alkyl ethanol ether sulfate, alkanolamide foam booster and magnesium and triethanolammonium ions
US5096622A (en) * 1988-12-05 1992-03-17 Colgate-Palmolive Company Liquid detergent composition containing alkylbenzene sulfonate, alkyl ethonal ether sulfate, alkanolamide foam booster and magnesium and triethanolammonium ions
US20070219112A1 (en) * 1996-11-26 2007-09-20 Singleton David M Highly branched primary alcohol compositions, and biodegradable detergents made therefrom

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4608197A (en) * 1984-06-25 1986-08-26 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from branched chain plasticizer alcohols
US4594185A (en) * 1984-06-25 1986-06-10 Atlantic Richfield Company Alkoxylated plasticizer alcohol ether sulfate surfactants
US4592875A (en) * 1984-06-25 1986-06-03 Atlantic Richfield Company Alkoxylated ether sulfate anionic surfactants from plasticizer alcohol mixtures
GB8420945D0 (en) * 1984-08-17 1984-09-19 Unilever Plc Detergents compositions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
GB485649A (en) * 1936-11-23 1938-05-23 Ig Farbenindustrie Ag Washing preparations
US2213477A (en) * 1935-12-12 1940-09-03 Gen Aniline & Film Corp Glycol and polyglycol ethers of isocyclic hydroxyl compounds
US2470719A (en) * 1945-05-26 1949-05-17 Nat Foam System Inc Stabilized foam-forming composition
US2506062A (en) * 1946-01-12 1950-05-02 Gen Aniline & Film Corp Fire extinguishing composition and method
US2562155A (en) * 1949-11-03 1951-07-24 American Cyanamid Co Wetting and detergent composition
GB874845A (en) * 1957-03-07 1961-08-10 Hispano Aviacion S A Means for controlling the stability of an aircraft

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
FR880343A (fr) * 1940-01-06 1943-03-23 Ig Farbenindustrie Ag Détersif

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2213477A (en) * 1935-12-12 1940-09-03 Gen Aniline & Film Corp Glycol and polyglycol ethers of isocyclic hydroxyl compounds
GB485649A (en) * 1936-11-23 1938-05-23 Ig Farbenindustrie Ag Washing preparations
US2470719A (en) * 1945-05-26 1949-05-17 Nat Foam System Inc Stabilized foam-forming composition
US2506062A (en) * 1946-01-12 1950-05-02 Gen Aniline & Film Corp Fire extinguishing composition and method
US2562155A (en) * 1949-11-03 1951-07-24 American Cyanamid Co Wetting and detergent composition
GB874845A (en) * 1957-03-07 1961-08-10 Hispano Aviacion S A Means for controlling the stability of an aircraft

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2908651A (en) * 1954-05-07 1959-10-13 Colgate Palmolive Co Liquid detergent composition
US2956947A (en) * 1957-08-06 1960-10-18 Union Carbide Corp Fire extinguishing method
US3055834A (en) * 1958-04-14 1962-09-25 Oreal Anhydrous anion-active detergents in the form of aerosols
US2970963A (en) * 1958-04-23 1961-02-07 Procter & Gamble Opaque liquid detergent composition
US3229777A (en) * 1961-03-22 1966-01-18 Swift & Co Method of transporting water from a well as a substantially stable foam
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3223186A (en) * 1962-05-23 1965-12-14 Pan American Corp Method of drilling with air or gas
US3320172A (en) * 1964-12-07 1967-05-16 Domtar Ltd Detergent composition
US3391750A (en) * 1965-08-09 1968-07-09 Union Carbide Corp Surfactant composition
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3852030A (en) * 1970-03-19 1974-12-03 Gaf Corp Surfactant for electrolyte-containing processing solutions
US4174291A (en) * 1972-04-28 1979-11-13 The Procter & Gamble Company Crystallization seed-containing composition
US3919125A (en) * 1972-05-23 1975-11-11 Nippon Unitol Co Ltd Method of preparing a highly concentrated solution of a higher secondary alcohol ethoxysulfate and such a concentrated solution
US3898186A (en) * 1973-04-09 1975-08-05 Procter & Gamble Dishwashing compositions containing gel forming gelatin
JPS502003A (fr) * 1973-05-08 1975-01-10
JPS5347807B2 (fr) * 1973-05-08 1978-12-23
US3910978A (en) * 1973-05-31 1975-10-07 Alcolac Inc Aqueous soluble mixed complex salts of aluminum aliphatic alcohol sulfates
US4077917A (en) * 1973-05-31 1978-03-07 Alcolac, Inc. Aqueous soluble mixed complex organic salts of aluminum sulfate
JPS5013403A (fr) * 1973-06-08 1975-02-12
JPS5412926B2 (fr) * 1973-06-08 1979-05-26
US3997692A (en) * 1974-09-16 1976-12-14 Lever Brothers Company Process of coating calcium sulfate dihydrate detergent filler particles
US3954649A (en) * 1974-09-16 1976-05-04 Lever Brothers Company Detergent compositions containing coated particulate calcium sulfate dihydrate
US4054541A (en) * 1974-11-04 1977-10-18 Witco Chemical Corporation Spray dried alcohol ether sulfate detergent compositions
JPS619354B2 (fr) * 1975-01-06 1986-03-22 Procter & Gamble
JPS51125405A (en) * 1975-01-06 1976-11-01 Procter & Gamble Semiipolar nonionic detergent and detergent composition containing alkali earth metal anion
US4075129A (en) * 1975-03-20 1978-02-21 Kao Soap Co., Ltd. Detergent composition
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US3998750A (en) * 1975-06-30 1976-12-21 The Procter & Gamble Company Liquid detergent composition
US4188311A (en) * 1975-07-24 1980-02-12 Chem-Y, Fabriek Van Chemische Produkten B.V. Detergent compositions containing ether sulfates
US4166048A (en) * 1975-09-22 1979-08-28 Kao Soap Co., Ltd. High foaming detergent composition having low skin irritation properties
US4299739A (en) * 1976-03-25 1981-11-10 Lever Brothers Company Use of aluminum salts in laundry detergent formulations
US4132680A (en) * 1976-06-24 1979-01-02 The Procter & Gamble Company Detergent compositions having soil release properties
US4129515A (en) * 1976-09-13 1978-12-12 The Procter & Gamble Company Heavy-duty liquid detergent and process
US4524002A (en) * 1983-02-23 1985-06-18 Gaf Corporation Foaming agent
US4699623A (en) * 1984-11-21 1987-10-13 Atochem Process of bleaching laundry
US4923635A (en) * 1987-07-06 1990-05-08 Colgate-Palmolive Company Liquid detergent composition containing alkylbenzene sulfonate, alkyl ethanol ether sulfate, alkanolamide foam booster and magnesium and triethanolammonium ions
US5096622A (en) * 1988-12-05 1992-03-17 Colgate-Palmolive Company Liquid detergent composition containing alkylbenzene sulfonate, alkyl ethonal ether sulfate, alkanolamide foam booster and magnesium and triethanolammonium ions
US20070219112A1 (en) * 1996-11-26 2007-09-20 Singleton David M Highly branched primary alcohol compositions, and biodegradable detergents made therefrom
US20080249336A1 (en) * 1996-11-26 2008-10-09 Singleton David M Highly branched primary alcohol compositions, and biodegradable detergents made therefrom
US7781390B2 (en) * 1996-11-26 2010-08-24 Shell Oil Company Highly branched primary alcohol compositions, and biodegradable detergents made therefrom
US7871973B1 (en) 1996-11-26 2011-01-18 Shell Oil Company Highly branched primary alcohol compositions, and biodegradable detergents made therefrom
US7888307B2 (en) * 1996-11-26 2011-02-15 Shell Oil Company Highly branched primary alcohol compositions, and biodegradable detergents made therefrom

Also Published As

Publication number Publication date
BE522826A (fr)
DE1013379B (de) 1957-08-08
FR1083752A (fr) 1955-01-12
GB738538A (en) 1955-10-12

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