US3223647A - Mild detergent compositions - Google Patents

Mild detergent compositions Download PDF

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Publication number
US3223647A
US3223647A US807333A US80733359A US3223647A US 3223647 A US3223647 A US 3223647A US 807333 A US807333 A US 807333A US 80733359 A US80733359 A US 80733359A US 3223647 A US3223647 A US 3223647A
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United States
Prior art keywords
alkyl
oxide
detergent
mildness
mixture
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Expired - Lifetime
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US807333A
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English (en)
Inventor
Howard F Drew
Jack G Voss
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.)
Procter and Gamble Co
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Procter and Gamble Co
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Filing date
Publication date
Priority to BE622461D priority Critical patent/BE622461A/xx
Priority to NL250152D priority patent/NL250152A/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US807333A priority patent/US3223647A/en
Priority to GB13097/60A priority patent/GB938988A/en
Priority to DEP24833A priority patent/DE1138497B/de
Priority to FR824621A priority patent/FR1301256A/fr
Priority to CH442860A priority patent/CH388511A/de
Application granted granted Critical
Publication of US3223647A publication Critical patent/US3223647A/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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • 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
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • This invention relates to combinations of synthetic detergents which have superior mildness characteristics. More particularly it relates to combinations of certain alkyl benzene sulfonates and tertiary amine oxides, which combinations are mild in their action toward the skin.
  • Alkyl benzene sulfonates having alkyl radicals ranging from about 9 to about 15 carbon atoms are widely used as household synthetic detergents. They are economical, and have good detergency, foaming, solubility, odor and color characteristics. However, in view of present day emphasis on mildness in detergent products and in view of published information (Schwartz, Perry and Berch, Surface Active Agents and Detergents, vol. ll, page 377) that these synthetics are less mild than soap, it is desirable that these alkyl benzene sulfonates be rendered as mild as possible to the human skin.
  • Tertiary amine oxides represented by the chemical formula (the oxygen being attached to the nitrogen by a semipolar bond), and conventionally indicated by the formula R R R N+ 0, wherein R is an alkyl radical containing about 10 to about 18 carbon atoms and R and R are each lower alkyl radicals, also are very efficient synthetic detergents with excellent detergency and foaming characteristics.
  • R is an alkyl radical containing about 10 to about 18 carbon atoms and R and R are each lower alkyl radicals
  • R and R are each lower alkyl radicals
  • the relative mildness to the human skin of the aforementioned alkyl benzene sulfonates and amine oxides can be determined by exaggerated exposures with test animals. In tests of extreme severity conducted on guinea pigs, for example, the alkyl benzene sulfonates and the amine oxides when used alone, cause a thickening of the skin of the test animal, usually accompanied by dryness and cracking of the skin.
  • the cleansing compositions of this invention having superior mildness characteristics comprise mixtures of alkyl benzene sulfonates having alkyl radicals ranging from about 9 to about 15 carbon atoms and tertiary amine oxides, having the formula R R R N O wherein R is an alkyl radical containing from about 10 to about 18 carbon atoms and R and R are each methyl, ethyl or propyl radicals, the ratio of the respective ingredients being in the range of about 20:1 to about 1:5, preferably about 10:1 to about 1:2.
  • the alkyl benzene sulfonates in the compositions of this invention are the water soluble salts, such as the alkali metal (e.g. sodium, potassium and lithium), ammonium and substituted ammonium (e.g. triethanolamine) salts, of sulfonated alkyl benzene in which the alkyl radicals range from about 9 to about 15 carbon atoms.
  • Alkyl benzene sulfonates usually contain mixtures of alkyl radicals in this range.
  • the preferred alkyl benzene sulfonate is one in which the alkyl radicals in the mixture average about 12 carbon atoms and are derived from a polypropylene which is predominantly tetrapropylene. This alkyl benzene sulfonate is hereinafter referred to as dodecyl benzene sulfonate and is most commonly used as a sodium salt.
  • Alkyl benzene sulfonates can be produced in a number of ways. The usual processes involve first the preparation of a satisfactory source for the alkyl component such as an olefin, e.g. polypropylene, or an alkyl halide, e.g. chlorinated kerosene. Alkyl benzene is formed by condensing the olefin or alkyl halide with benzene in a reaction of the Fried-el-Crafts type using a catalyst such as Alclg or HP. The alkyl benzene is then sulfonated, purified, converted to the desired salt and worked up to the desired form, e.g. powder, granule or paste. The manufacture of alkyl benzene sulfonates is described in the Journal of the American Oil Chemists Society, 35, 520 24 and 528-31 (1958).
  • the tertiary amine oxides in the compositions of this invention have the formula R R R N O wherein R is an alkyl radical containing from about 10 to about 18 carbon atoms, and R and R are each methyl, ethyl or propyl radicals. If R is shorter in chain length than about 10 carbon atoms, the solubility of the resulting amine oxide is reduced. If R is longer in chain length than about 18 carbon atoms, .the solubility of the resulting amine oxide is reduced to an undesirable point for detergency purposes. Amine oxides in which R, contains 12 to 16 carbon atoms have preferred solubility, foaming and detergency characteristics, particularly when R is a straight, saturated chain.
  • R and R are longer in chain length than 3 carbon atoms, the resulting amine oxide is not sufficiently soluble to be desirable as a detergent.
  • Those higher alkyl tertiary amine oxides in which R and R are methyl radicals also have preferred detergen-cy, solubility and foaming characteristics for use in this invention.
  • the lauryl dialkyl amine oxides and those tertiary amine oxides in which the R alkyl radicals are predominantly the mixture of lauryl and myristyl radicals found in fractionated coconut oil fatty alcohol are particularly desirable compounds in the compositions of the present invention.
  • the higher alkyl tertiary amine oxides of this invention can be produced by oxidizing higher alkyl tertiary amines with an oxidizing agent such as hydrogen peroxide or Caros reagent (ammonium or potassium persulfate dissolve-d in concentrated sulfuric acid).
  • oxidizing agent such as hydrogen peroxide or Caros reagent (ammonium or potassium persulfate dissolve-d in concentrated sulfuric acid).
  • Higher alkyl tertiary amines can be produced by alkylating a secondary amine; for example, lauryl dimethyl amine can be produced by reacting dimethyl amine with lauryl alcohol or a derivative thereof such as lauryl iodide.
  • Examples of the higher alkyl groups in the tertiary amine oxides which can be used in the compositions of this invention include primary alkyl groups such as cetyl and oleyl groups which are derived from fats and oils or petroleum derived olefins, secondary alkyl groups such as an m-methyl pentadecyl group derived from an a-olefin, substituted alkyl groups such as a 2 hydroxylauryl group, and non-aromatic interrupted alkyl groups such as a carb-amide substituted alkyl group.
  • primary alkyl groups such as cetyl and oleyl groups which are derived from fats and oils or petroleum derived olefins
  • secondary alkyl groups such as an m-methyl pentadecyl group derived from an a-olefin
  • substituted alkyl groups such as a 2 hydroxylauryl group
  • non-aromatic interrupted alkyl groups such as a carb-amide substituted alky
  • amine oxides which can be used in preparing the compositions of the present invention are:
  • Lauryl dimethylamine oxide Myristyl d-imethylamine oxide Cetyl dimethylamine oxide Z-hydroxylauryl dimethyla-mine oxide u-M-ethylundecyl dimethylamine oxide Oleyl dimethylamine oxide Lauryl methyl ethyl amine oxide Lauryi diethylamine oxide Z-diethyl amino ethyl lauramide oxide Myristyl diethylamine oxide Cetyl diethylamine oxide a-Met'hylpentadecyl diethylamine oxide Oleyl diethylamine oxide Myristyl ethyl propyl amine oxide Lauryl dipropylamine oxide Myristyl dipropylamine oxide Cetyl dipropylamine oxide Cetyl methyl propyl amine oxide Coconut alkyl dime'thylamine oxide wherein the higher alkyl radicals are predominantly the mixture of lauryl and myristyl radicals found in coconut oil fatty alcohol (such a mixture can
  • coconut oil alkyl sulfates like alkyl benzene sulfonates, are widely used synthetic detergents which reportedly could be made mild-er.
  • grade 10 represents ideal or perfect skin (soft, smooth and flexible) and the effect of a theoretically perfectly mild detergent; grade 1 represents severely irritated skin. Other values represent gradation-s of severity between these extremes.
  • Grade 1 in a guinea pig immersion test indicates severely thickened, dry, cracked and bleeding skin, i.e. extreme irritation.
  • Grade 1 in exaggerated tests on human subjects indicates severe redness and dryness of the skin. Thus, the exaggerated exposure tests on animals are much more extreme than those conducted on human subjects.
  • the graded guinea pig immersion tests consist of immersing the animal up to the thorax in the test solutions at 37 C. for a 4 /2 hour period per day for 3 consecutive days. The animals are graded 3 days after the last immersion. The grades given in the examples are the average of the results on not less than three animals.
  • Example I The following aqueous solutions were compared in graded guinea pig immersion tests:
  • Example 11 The following aqueous solutions were compared in graded guinea pig immersion tests:
  • Ratio, Alkylbenzene Sulfonate Amine Oxide Test Solution Grade 0.2% sodium dodeeyl benzene sultan-ate" 0.2% sodium alkyl benzene sult'onate (the alkyl group being derived from a mixture of straight chain olefins averaging 12 carbon atoms).
  • Test solution Grade 0.2% sodium salt of sulfated coconut oil fatty alcohol 0.2% sodium salt of sulfated coconut oil fatty alcohol+0.l% lauryl dimethyl amine oxide 5 6
  • Example IV An exaggerated arm washing exposure test was conducted on human subjects using two 10% solutions (A and B) of a granular detergent having the following compositions:
  • Solution A consisted of the granular detergent composition alone.
  • Solution B an amount of lauryl dimethyl amine oxide equal to 10% by weight of the detergent composition in solution was added.
  • the solutions were used at 105 F.
  • Ten human subjects participated in the test.
  • the inner aspects (inside) of each elbow of each subject were Washed with the solutions, one aspect with Solution A, the other with Solution B.
  • the test consisted of rubbing the aspects for 30 seconds with a 4 inch square terry cloth wash cloth saturated with the test solution.
  • the solution was allowed to remain on the subjects arm for an additional 30 seconds and the arm was then blotted dry.
  • This washing test was conducted on each subject three times daily, morning, midday and afternoon, for three days. The subjects were graded after the final washing on a l to 10 scale as described above.
  • the mild mixtures of alkyl benzene sulfonates and amine oxides in the compositions of this invention are useful as detergents per se or in combination with any of the usual synthetic detergent adjuvants, builders, diluents and additives to produce mild detergent products such as heavyor light duty detergent granules, heavy and light duty liquid detergents, shampoos or detergent bar-s.
  • the mildness characteristics of the mixtures of alkyl benzene sulfonates and amine oxides of the present invention are useful in any detergent or cleansing composition which comes in contact with the skin in an aqueous medium.
  • Detergent compositions containing the synthetic detergent mixture of this invention can comprise from about 0.5% to of the mixture as an essential detergent and sudsing component depending on the end use.
  • a scouring cleanser can contain as little as about 0.5% of the detergent mixture of this invention or a dry granular detergent composition comprising 100% of the mixture can be used to make a washing solution.
  • the composition containing the mixture of the invention is milder to the skin during use than an equal amount of either of the individual components of the mixture alone.
  • Detergent compositions usually contain about 5% to about 50% synthetic detergent, i.e. the mixture of alkyl benzene sulfonates and amine oxides described in this invention.
  • Amine oxides are advantageously combined with alkyl benzene sulfonates not only for the unexpected mildness which is effected in the combination but for additional qualities which amine oxides impart to alkyl benzen sulfonate compositions.
  • Example VI A mild, light-duty, granular detergent composition of excellent efficiency is made by mixing together the following ingredients:
  • Example VII A mild efiicient liquid dishwashing detergent which foams well is made by mixing together the following ingredients:
  • a mild efl'icient detergent toilet bar is made by dry mixing, milling, extruding and stamping into a bar the following ingredients:
  • Example X A mild scouring cleanser which foams and cleans well is made by mixing together the following ingredients:
  • silica flour 13 parts trisodium phosphate 1 part sodium dodecylbenzene sulfonate 1 part myristyl diethylamine oxide
  • a composition capable of synergistic mildness when used as an active ingredient in a detergent composition said composition being a mixture-of a water soluble alkyl benzene sulfonate having an alkyl radical ranging from about 9 to about 15 carbon atoms and a tertiary amine oxide having the formula R R R O wherein R is an alkyl radical containing from about 10 to about 18 carbon atoms and R and R are each selected from the group consisting of methyl, ethyl and propyl radicals, the ratio of alkyl benzene sulfonate to tertiary amine oxide being in the range of about 10:1 to about 1:2.
  • composition of claim 1 wherein R and R are methyl radicals and R is a straight saturated chain of from 12 to 16 carbon atoms.
  • a mild liquid detergent composition consisting essentially of about 5% to about 50% of the mixture of claim 1 in an aqueous vehicle.
  • a mild granular detergent composition consisting essentially of about 5% to about 50% of the mixture of claim 1, sodium tripolyphosphate and sodium sulfate.
  • a mild liquid detergent composition consisting essentially of about 5% to about 50% of the mixture of claim 2, water and ethanol.
  • composition of claim 6 wherein the alkyl benzene sulfonate is sodium dodecyl benzene sulfonate.
  • a composition capable of synergistic mildness when used as an active ingredient in a detergent composition said composition being a mixture of about equal parts of sodium dodecylbenzene sulfonate and lauryl dimethyl amine oxide.
  • a detergent composition consisting essentially of a mixture of about equal parts of a water soluble dodecyl benzene sulfonate and dodecyl dimethyl amine oxide, said mixture being capable of synergistic mildness.

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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)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Detergent Compositions (AREA)
US807333A 1959-04-20 1959-04-20 Mild detergent compositions Expired - Lifetime US3223647A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE622461D BE622461A (en)) 1959-04-20
NL250152D NL250152A (en)) 1959-04-20
US807333A US3223647A (en) 1959-04-20 1959-04-20 Mild detergent compositions
GB13097/60A GB938988A (en) 1959-04-20 1960-04-12 Detergent compositions
DEP24833A DE1138497B (de) 1959-04-20 1960-04-14 Synthetisches, hautschonendes Wasch- und Reinigungsmittel
FR824621A FR1301256A (fr) 1959-04-20 1960-04-15 Composition détersive présentant des caractéristiques de grande douceur pour la peau
CH442860A CH388511A (de) 1959-04-20 1960-04-20 Wasch- und Reinigungsmittel

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US807333A US3223647A (en) 1959-04-20 1959-04-20 Mild detergent compositions

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CH (1) CH388511A (en))
DE (1) DE1138497B (en))
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NL (1) NL250152A (en))

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3309319A (en) * 1965-09-23 1967-03-14 Procter & Gamble Detergent-whitener compositions
US3388069A (en) * 1964-01-04 1968-06-11 Henkel & Cie Gmbh Liquid active oxygen detergent bleaching concentrate
US3424849A (en) * 1965-07-13 1969-01-28 Procter & Gamble Bath oil composition containing octyl dodecanoate
US3470102A (en) * 1965-01-22 1969-09-30 Lever Brothers Ltd Detergent composition
US3642506A (en) * 1969-11-28 1972-02-15 Swift & Co Method for improving the properties of hydraulic cementitious mixtures
US3867549A (en) * 1969-02-10 1975-02-18 Colgate Palmolive Co Stable starch compositions
US4033895A (en) * 1975-12-24 1977-07-05 Revlon, Inc. Non-irritating shampoo compositions containing stearyl amine oxide
US4113631A (en) * 1976-08-10 1978-09-12 The Dow Chemical Company Foaming and silt suspending agent
US4306999A (en) * 1979-11-23 1981-12-22 American Can Company High solids, low viscosity lignin solutions
US4741863A (en) * 1984-02-10 1988-05-03 Toyota Jidosha Kabushiki Kaisha Alkaline degreasing solution comprising amine oxides
US4839158A (en) * 1986-02-25 1989-06-13 E. B. Michaels Research Associates Inc. Process and composition for oral hygiene
US5041243A (en) * 1989-10-30 1991-08-20 Colgate-Palmolive Company Laundry bar
US5055233A (en) * 1989-04-26 1991-10-08 Ethyl Corporation Detergent bar process using trialkylamine oxide dihydrate
US5082600A (en) * 1989-04-26 1992-01-21 Ethyl Corporation Transparent soap bar process using trialkylamine oxide dihydrate
US5096621A (en) * 1989-04-19 1992-03-17 Kao Corporation Detergent composition containing di-long chain alkyl amine oxides
US5275804A (en) * 1986-02-25 1994-01-04 E. B. Michaels Research Associates, Inc. Process and composition for oral hygiene
US5389676A (en) * 1991-03-22 1995-02-14 E. B. Michaels Research Associates, Inc. Viscous surfactant emulsion compositions
WO1996013565A1 (en) * 1994-10-28 1996-05-09 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
US5691291A (en) * 1994-10-28 1997-11-25 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
US5905065A (en) * 1995-06-27 1999-05-18 The Procter & Gamble Company Carpet cleaning compositions and method for cleaning carpets
US6035869A (en) * 1997-09-10 2000-03-14 Albemarle Corporation Dish-washing method
US6297278B1 (en) 1991-03-22 2001-10-02 Biosyn Inc. (A Pennsylvania Corporation) Method for inactivating sexually transmitted enveloped viruses
US6323170B1 (en) 1994-10-28 2001-11-27 The Procter & Gamble Co. Floor cleaners which provide improved burnish response
US20060257282A1 (en) * 2005-05-12 2006-11-16 Tony Buhr Large-scale decontamination of biological microbes using amine oxides at acidic pH

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5655498A (en) * 1979-10-11 1981-05-16 Lion Corp Detergent composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB437566A (en) * 1934-02-16 1935-10-31 Chem Ind Basel Manufacture of textile assistants
US2060568A (en) * 1934-06-23 1936-11-10 Soc Of Chemical Ind Assisting agents for the textile industry
US2169976A (en) * 1934-01-26 1939-08-15 Ig Farbenindustrie Ag Process of producing assistants in the textile and related industries
US2477383A (en) * 1946-12-26 1949-07-26 California Research Corp Sulfonated detergent and its method of preparation
CA503047A (en) * 1954-05-25 Gotte Ernst Skin protecting agent

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA503047A (en) * 1954-05-25 Gotte Ernst Skin protecting agent
US2169976A (en) * 1934-01-26 1939-08-15 Ig Farbenindustrie Ag Process of producing assistants in the textile and related industries
GB437566A (en) * 1934-02-16 1935-10-31 Chem Ind Basel Manufacture of textile assistants
US2060568A (en) * 1934-06-23 1936-11-10 Soc Of Chemical Ind Assisting agents for the textile industry
US2477383A (en) * 1946-12-26 1949-07-26 California Research Corp Sulfonated detergent and its method of preparation

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3388069A (en) * 1964-01-04 1968-06-11 Henkel & Cie Gmbh Liquid active oxygen detergent bleaching concentrate
US3470102A (en) * 1965-01-22 1969-09-30 Lever Brothers Ltd Detergent composition
US3424849A (en) * 1965-07-13 1969-01-28 Procter & Gamble Bath oil composition containing octyl dodecanoate
US3309319A (en) * 1965-09-23 1967-03-14 Procter & Gamble Detergent-whitener compositions
US3867549A (en) * 1969-02-10 1975-02-18 Colgate Palmolive Co Stable starch compositions
US3642506A (en) * 1969-11-28 1972-02-15 Swift & Co Method for improving the properties of hydraulic cementitious mixtures
US4033895A (en) * 1975-12-24 1977-07-05 Revlon, Inc. Non-irritating shampoo compositions containing stearyl amine oxide
US4113631A (en) * 1976-08-10 1978-09-12 The Dow Chemical Company Foaming and silt suspending agent
US4306999A (en) * 1979-11-23 1981-12-22 American Can Company High solids, low viscosity lignin solutions
US4741863A (en) * 1984-02-10 1988-05-03 Toyota Jidosha Kabushiki Kaisha Alkaline degreasing solution comprising amine oxides
US4839158A (en) * 1986-02-25 1989-06-13 E. B. Michaels Research Associates Inc. Process and composition for oral hygiene
US5275804A (en) * 1986-02-25 1994-01-04 E. B. Michaels Research Associates, Inc. Process and composition for oral hygiene
US5096621A (en) * 1989-04-19 1992-03-17 Kao Corporation Detergent composition containing di-long chain alkyl amine oxides
US5055233A (en) * 1989-04-26 1991-10-08 Ethyl Corporation Detergent bar process using trialkylamine oxide dihydrate
US5082600A (en) * 1989-04-26 1992-01-21 Ethyl Corporation Transparent soap bar process using trialkylamine oxide dihydrate
US5041243A (en) * 1989-10-30 1991-08-20 Colgate-Palmolive Company Laundry bar
US5389676A (en) * 1991-03-22 1995-02-14 E. B. Michaels Research Associates, Inc. Viscous surfactant emulsion compositions
US6297278B1 (en) 1991-03-22 2001-10-02 Biosyn Inc. (A Pennsylvania Corporation) Method for inactivating sexually transmitted enveloped viruses
WO1996013565A1 (en) * 1994-10-28 1996-05-09 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
US5691291A (en) * 1994-10-28 1997-11-25 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
US6323170B1 (en) 1994-10-28 2001-11-27 The Procter & Gamble Co. Floor cleaners which provide improved burnish response
US5905065A (en) * 1995-06-27 1999-05-18 The Procter & Gamble Company Carpet cleaning compositions and method for cleaning carpets
US6035869A (en) * 1997-09-10 2000-03-14 Albemarle Corporation Dish-washing method
US20060257282A1 (en) * 2005-05-12 2006-11-16 Tony Buhr Large-scale decontamination of biological microbes using amine oxides at acidic pH

Also Published As

Publication number Publication date
NL250152A (en))
DE1138497B (de) 1962-10-25
BE622461A (en))
GB938988A (en) 1963-10-09
CH388511A (de) 1965-02-28

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