US3234139A - Diamine dioxide detergent compositions - Google Patents

Diamine dioxide detergent compositions Download PDF

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Publication number
US3234139A
US3234139A US335373A US33537364A US3234139A US 3234139 A US3234139 A US 3234139A US 335373 A US335373 A US 335373A US 33537364 A US33537364 A US 33537364A US 3234139 A US3234139 A US 3234139A
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Prior art keywords
dioxide
detergent
diamine
water
trimethyl
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US335373A
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English (en)
Inventor
Howard F Drew
Roger E Zimmerer
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to NL286808D priority Critical patent/NL286808A/xx
Priority to BE626346D priority patent/BE626346A/xx
Priority claimed from US161307A external-priority patent/US3197509A/en
Priority to FR919218A priority patent/FR1347955A/fr
Priority to GB48383/62A priority patent/GB1007343A/en
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US335373A priority patent/US3234139A/en
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • 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
    • C11D3/06—Phosphates, including polyphosphates

Definitions

  • This invention relates to detergent compounds and com positions and more particularly to new and novel surface active diamine dioxides and compositions composed thereof.
  • An advantageous property for an organic detergent is a low degree of hygroscopicity which results in improved crystallinity.
  • detergent surface active agents which are hygroscopic are used in bar or granular forms desirable physical properties are impaired. Bars become soft and slimy and granules tend to cake and lose their free flowing and quick dissolving characteristics.
  • trialkylamine oxides have been found to be excellent detergent compounds but are so hygroscopic that they can be effectively used only in liquid detergent compositions.
  • a high degree of aqueous solubility is desirable since some well-known surface active agents such as akylbenzenesulfonate are very insoluble in water in the presence of other electrolytes and can only be used in liquid detergent compositions in conjunction with a suitable hydrotrope such as toluene sulfonate.
  • a high degree of detergency in cool or cold water is also highly desirable. Many fabrics such as those containing crease resistant additives should be washed in cool water to retain their crease resistant properties. Wool garments should be Washed in cool water. In some locations Warm or hot water is not available.
  • Detergent surface active agents which exhibit a high degree of mildness are particularly desirable.
  • the diamine dioxides of this invention are:
  • R is an alkyl group having from to 18 carbon atoms; R R and R each are methyl, ethyl or propyl radicals and n is the Whole number 2 or 3.
  • the arrows are the conventional representation for semipolar bonds.
  • Tertiary amine oxides as a broad class of compounds are known.
  • diamine dioxides are new and novel. It is surprising to find in this new and novel class of compounds, compounds which have highly desirable properties as organic detergents.
  • R R or R are alkyl radicals containing more than three carbon atoms, the compounds begin to lose their high solubility in the presence of an electrolyte. The nonhydroscopic properties of these compounds are also adversely affected. Surprisingly, those compounds containing one or more methyl groups have been found to exhibit especially outstanding sudsing properties.
  • the R alkyl group can be derived from naturally occurring fats and oils or from synthetic sources. Mixtures of diamine dioxides are very suitable wherein R varies in chain length from about C to C In the solid compositions, particularly granular products, an octadecylethylene or octadecyl trimethylene diamine dioxide or the tallow alkyl homologue thereof is preferred.
  • the preferred compound for use in liquid compositions is the corresponding dodecyl or coco alkyl homologue thereof.
  • the diamine dioxides of this invention can be prepared by oxidizing corresponding diamines.
  • a corresponding primary aliphatic diamine in general, can be prepared by the method disclosed in US. Patent 2,754,330.
  • Primary aliphatic diamines are prepared from glycols or amino alcohols by reacting the alcoholic compound with ammonia over a ruthenium catalyst.
  • Compounds of this invention are useful per se as detergents and surface active agents. Desirably, they are used with other materials to form built and unbuilt liquid and solid compositions, as for example, bar, flake, granular or tabletted granular compositions. It has been found in the liquid compositions built with a pyrophosphate compound, that N,N',N' trimethyl-N-dodecylethylenediamine-N,N'-dioxide gives the most unusual and desirable results. On the other hand, N,N, trimethyl-N-octadecyletliylenediamine-N,N'-dioxide gives unusual and outstanding results in a granular or other solid product.
  • the solid form detergent compositions of this invention can contain from about 5% to of the instant diamine dioxides and from 95% to about 20% of normally solid anionic organic detergents, nonionic organic detergents, water soluble inorganic alkaline buildersalts, water soluble organic alkaline sequestrant builders salts and mixtures thereof.
  • the liquid compositions of this invention contain in addition to these other actives and additives from about 2% to about. 30% of the diamine' dioxides of this invention in a liquid vehicle.
  • Granular or flake detergents preferably contain about 5% to about 50% of the diamine dioxides of this invention and from about 95% to about 50% normally solid, water soluble inorganic alkaline builder salts, or organic.
  • Anionic organic detergents used alone or in admixture include both the soap and non-soap detergents.
  • suitable soaps are the sodium,-potassium, ammonium. and alkylolammonium salts of higher fatty acids (C -C Particularly useful are the sodiumand potassium salts of the mixtures of fatty acids derivedfrom coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
  • anionic organic nonsoap detergents are: alkyl glyceryl ether sulfonates; alkyl sulfates; alkyl monoglyceride sulfates or-sulfonates; alkyl polyethenoxy ether sulfates; acyl sarcosinates; acyl esters of isethionates; acyl N-methyl taurides; alkylbenzenesul-i fonates; alkyl phenol polyethenoxy sulfonates.
  • alkyl andacyl groups respectively, contain to carbon atoms. They are used in the form oxide and ethylene diamine wherein the molecular weight.
  • condensation products range from 5000 to 11,000; the condensation product of from about 5 to 30 moles of ethylene oxide with one mole of a straight or branched. chain aliphatic alcohol containing from 8 to 18 carbon;
  • atoms e.g., lauryl alcohol
  • Water-soluble inorganic alkaline builder salts used alone or in admixture are alkali metalcarbonates, borates, phosphates, polyphosphates, bicarbonates and silicates.
  • Ammonium or substituted ammonium salts can also be used. Specific examples of such salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate,
  • tripolyphosphate potassium pyrophosphate, sodium hexametaphosphate, sodium sesquicarbonate, sodium monoand di-ortho phosphate and potassium bicarbonate- .Such a inorganic builder salts enhance the detergency of the subject diamine dioxides.
  • Water-soluble organic alkaline sequestrant builder salts used alone or in admixture are alkali metal,
  • alkali metal salts of phytic acid e.g., sodium phytate Mixed salts of these polycarboxylates are also suitable. .
  • alkali metal salts of phytic acid e.g., sodium phytate Mixed salts of these polycarboxylates are also suitable. . The.
  • the preferred solid form detergent compositions con-..
  • the tain about. 10% to about 30% ofthe diamine dioxides of the invention andat least an equal amount of sodium tripolyphosphate.
  • the higher alkyl dia'mine di oxides wherein the .alkyl radical ranges from 16 to 18 carbon atoms in.chain length are used insuch preferred compositions.
  • the preferred built liquid detergent compositions contain about 5% to about 30% .of the diamine dioxides-of the invention and about 5% to 40% ofpotassiumpyrophosphate in a liquid vehicle.
  • the detergent compositions. of this invention canconv tain any of the ,usual adjuvants, diluents: and additives,- for example, ampholytic or .zwitterionic detergents, cationic detergents, perfumes, anti-tarnishing; agents, anti-' redeposition agents, bacteriostatic agents, dyes, fluorescers, oxygen or chlorine .bleaches, suds bui1ders, suds depressors, and the like.
  • Thefollowing examples illustrate the preparation of diaminedioxides compounds" and ,compositionsof this invention.
  • a reflux condenser was installed; A vigorous reactionensued-accompanied by considerable foaming. This was controlled by periodic cooling to about 90 C. in a cold water bath. Reflux temperature (100 C.) was maintained until the evolution of CO had almost ceased (3 /2 days).
  • the mixture was combined with 150 mls. of concentrated HCl and heated to 100 C. on the steam bath to remove excess formaldehyde and formic acid.
  • the solution was made basic with 30% aqueous sodium hydroxide solution, the layer of amine separated and distilled through a 1 foot Vigreux column at a pressure of 1 mm. of mercury. The fraction boiling from 130135 C. with 11 1.4475 was collected. This fraction weighed 71 grams representing a yield 64% of theory for N,N,N'-trimethyl-N-dodecylethylenediamine.
  • the spent catalyst was removed by filtration and the unreacted amine (1.3 grams) was removed by a triple extraction with petroleum ether.
  • the alcohol was removed on the steam bath under a current of nitrogen.
  • the residual solution was freeze-dried to yield 45 grams of hydrated N,N',N' trimethyl N dodecylethylenediamine N,N- dioxide representing a 94% yield.
  • N,N-diethylethylenediamine for N,N- dimethylethylenediamine as the starting material in this example, N,N'-diethyl-N-methyl-N-dodecylethylenediamine-N,N'-dioxide was obtained.
  • EXAMPLE II In a 5-liter, B-necked, glass, round-bottom flask equipped with a reflux condenser, addition funnel, and mechanical stirring assembly were placed 300 grams (5 moles) ethylenediamine, obtained from Matheson, Coleman and Bell, dissolved in 150 mls. of formula 3A alcohol. This solution was stirred while 333 grams (1 mole) of octadecyl bromide dissolved in 2 liters of formula 3A alcohol were added over a period of 1 /2 hours. The temperature was raised to a reflux (77 C.) by means of an electric heating mantle. Stirring and heating were continued for about 6 hours. At this point 1000 mls.
  • the resulting solution was poured into a mixture of 1000 grams of crushed ice and 400 mls. of 30% aqueous sodium hydroxide solution.
  • the solids were removed by filtration, taken up in ether, washed with water, and the ether removed by evaporation on a steam bath.
  • the resulting dark brown product consisted of 51 grams of liquid and 62 grams of paste-like solid. Infrared spectra indicated the liquid was completely methylated (no N-H bands were detected) while the solid was incompletely methylated.
  • the liquid portion was distilled at 0.1 mm. mercury pressure through a 1 ft. Vigreux column to yield 30 grams boiling from 156- 161 C. with n 1.4532.
  • N,N- diethylethylenediamine obtained from Eastman Kodak Co., was converted to N',N-diethyl-N-dodecylethylenediamine following the procedure given in Example I.
  • This amine was convert-ed to N,N,N-triethyl- N-dodecylethylenediamine in a manner analogous to the methylation in Example I except that acetaldehyde was used in place of formaldehyde.
  • the oxidation was carried out in the same manner as above to give N,N',N'- triethyl-N-dodecylethylenediamine-N,N'-dioxide.
  • N,N,N' tripropyl-N-tetradecylethylenediamine-N,N- dioxide was prepared in a manner analogous to that given in Example If except that tetradecyl bromide and propionaldehyde were substituted for octadecyl bromide and formaldehyde respectively.
  • N,N,N trimethyl N dodecylethylenediamine-N,N'- dioxide prepared in the manner described in Example I, was determined to be substantially superior to sodium dodecylbenzenesulfonate wherein the dodecyl group was derived from tetrapropylene in the cloth-swatch deterency test described below.
  • Sodium dodecylbenzenesulfonate is a widely used detergent active for laundering compositions and is, therefore, a reasonable standard for comparison.
  • This test involved washing naturally soiled cloth (desized print cloth) in a 0.1% aqueous solution of a comosition com risin 20% or anic deter ent com ound (diamine dioxide being tested or the alkylbenzenesulfonate standard), 50% sodium tripolyphosphate and 30% sodium sulfate. and the washing was done at 140 F. for minutes using wash water of 7 grains per gallon hardness.
  • the detergency effectiveness was determined by measuring the percentage of lipid soil remaining on a standard size swatch (on a dry basis) after the washing operation. The percentage of lipid soil remaining after washing with the diamine dioxide test composition was compared with the percentage after washing with the alkylbenzene sulfonate standard composition.
  • the composition had a pH of 10.0
  • the hygroscopicity of N,N,N'-trimethyl N dodecyl- I ethylenediamine-N,N-dioxide was determined by exposing dry recrystallized material in a constant 50% relative humidity chamber at 70 B; it had weight increases of about 4.0% after 2 days and about 15% after 7 days in this hygroscopicity test.
  • ide a known detergent active, had weight increases of 32% after 1 day and 30% after 7 days. It is apparent that the former compound is much less hygroscopic than the latter;
  • N,N,N-trimethyl-N dodecylethylenediamine N,N'- dioxide has'been found to exhibit an unexpectedly high degree of mildness. It is also an effective mildness additive for other detergents. On a comparative basisin a standard, but exaggerated, mildness test, using guinea pigs with shaved undersides, partially immersed in aqueous.
  • the washing solutions used in the. wash-Wear test contain 0.03% organic detergent compound and 0.06% sodi um tripolyphosphate. (No fluorescers, bleaches, or antiredeposition agents are used.)
  • The, pH of the washing solution is 10 and water. of 7 grains per gallon hardness is used.
  • a conventional, agitator-type washer and wash water of 130 F. are vused.
  • the detergent compound in the standard detergent composition is sodium dodecylbenzenesulfonate, the most commonly used organic detergent surfaceactive agent in heavy duty laundry detergent'compositions.
  • Thetest detergent composition con test solutions N,N,N-trimethyl N-dodecylethylenedi- 1 amine-N,N-dioxide was scored as an 8 on a scale of 1 to 10 wherein the highest score indicates the highest degree of desirable mildness and 1 is severe irritation.
  • Sodium dodecylbenzenesulfonate was scored as 4.
  • At least three or more test solutions of 0.2% detergent active were averaged in tabulating the results.
  • the solubility of N,N',N-trimethyl-N-dodecylethylenediamine-N,N-dioxide in aqueous electrolyte solutions was determined by adding known amounts of diamine dioxide to known amounts of tetrapotassium pyrophosphate and tetrapotassium ethylenediamine tetraacetate (Ki EDTA). No hydrotroping agents were used. It was foundthat 100 grains of 20% aqueous K EDTA at roorntemperature. In the case of K pyrophosphate, the results showed that more than 16 grams of diamine dioxide were soluble in 100 grams of 20% aqueous electrolyte. The generally high solubility of the diamine dioxide in aqueous solutions of electrolyte is apparent from the solubility of.
  • N,N-dioxide has performance characteristics.snbstantially similar in all respects tothose of. N,N,N--trimethyl- N dodecylethylenediamine- N,Ndioxide.
  • the other. diamine dioxides of this invention will have substantially An aqueous test L more than 21 grams of diamine dioxide were soluble in tains the detergent compound to the compared with the detergent compound in the standard compositions.
  • N,N',N'-trimethyl-N-octadecylethylenediamine-N,N-dioxide was preferred over the standard test composition in general, detergency eifectiveness.
  • the surprising cool water detergency powers of .the diamine dioxides of this invention was demonstrated by the results obtained in the swatch test of Example Vl wherein the test swatches were washed in aqueoussolution containing sodium dodecylbenzenesulfonate at 140 F.” for 10 minutes 'and aqueous solution containing- N,N',N trimethyl-N-octadecylethylenediamine N,N'- dioxide ,at F: for 10 minutes.
  • the percentage of lipid soil remaining on the swatches after washing with the diamine dioxide solution at low temperature is found to be about equivalent to. that remaining after washing with the sodium dodecylbenzenesulfonate standard composition at- 140 'F.
  • the diaminedioxides-of-this invention can be usedin effective solid 'form detergent compositions having. improved hygroscopicity, desirable mildness and ,detergency efiicacy.
  • the :following formulations have these characteristics:
  • Liquid form detergent compositions provide convenience in use, particularly for measurement and dispensing operations.
  • Liquid detergent compositions can 40 be in the form of solution, dispersions or emulsions.
  • they can contain from about 5% to about 30% of the diamine dioxides of this invention and from about 5% to about 40% of a water-soluble inorganic alkaline builder salt or an organic alkaline sequestrant builder salt, the balance of the composition being a solvent, such as water, and/or other liquid vehicles.
  • liquid detergent compositions including the diamine dioxides of'this invention are as follows:
  • this invention is not limited to the specific embodiments or specific examples thereof except as defined in the appended claims.
  • a detergent composition consisting essentially of from about 5% to about of N,N',N-trimethyl-N- alkylethylenediamine-N,N-dioxide wherein said alkyl ranges in chain length from 10 to 18 carbon atoms and about to about 20% of a builder selected from the group consisting of water-soluble inorganic alkaline builder salts, Water-soluble organic alkaline sequestrant builder salts, and mixtures thereof.
  • a detergent composition in solid form consisting essentially of from about 5% to about 50% of N,N,N- trimethyl-N-alkylethylenediarnine-N,N-dioxide wherein said alkyl ranges in chain length from 10 to 18 carbon atoms and about 95% to about 50% of a normally solid builder selected from the group consisting of water-soluble inorganic alkaline builder salts, Water-soluble organic alkaline sequestrant builder salts, and mixtures thereof.
  • a detergent composition in solid granular form consisting essentially of from about 5% to about 50% of N,N',N trimethyl N alkyletl-lylenediamine N,N- dioxide wherein said alkyl ranges in chain length from 10 to 18 carbon atoms and about 95% to about 50% sodium tripolyphosphate.
  • a detergent composition in solid granular form consisting essentially of from about 5% to about 50% of N,N',N trimethyl N octadecylethylenediamine- N,N-dioxide and about 95 to about 50% sodium tripolyphosphate.
  • a liquid detergent composition consisting essentially of from about 5% to about 30% of N,N,N-triinethyl- N-dodecylethylenediamine-N,N'-dioxide; and about 5% to about 40% potassium pyrophosphate; balance Water.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
US335373A 1961-12-21 1964-01-02 Diamine dioxide detergent compositions Expired - Lifetime US3234139A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL286808D NL286808A (is") 1961-12-21
BE626346D BE626346A (is") 1961-12-21
FR919218A FR1347955A (fr) 1961-12-21 1962-12-19 Nouveaux détergents à base de dioxydes de diamine
GB48383/62A GB1007343A (en) 1961-12-21 1962-12-21 Amine oxide detergents
US335373A US3234139A (en) 1961-12-21 1964-01-02 Diamine dioxide detergent compositions

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US161307A US3197509A (en) 1961-12-21 1961-12-21 Diamine dioxide compounds
US335373A US3234139A (en) 1961-12-21 1964-01-02 Diamine dioxide detergent compositions

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2215371A1 (de) * 1971-04-02 1972-10-19 Unilever N.V., Rotterdam (Niederlande) Waschmittel
EP0042188A1 (en) * 1980-06-17 1981-12-23 THE PROCTER & GAMBLE COMPANY Detergent composition containing low levels of amine oxides
US4391726A (en) * 1980-11-28 1983-07-05 The Procter & Gamble Company Detergent composition containing low levels of amine oxides
US4588522A (en) * 1982-04-24 1986-05-13 Hoechst Aktiengesellschaft Betaine-amine oxides, a process for their preparation and their use as surfactants
WO1995016016A1 (en) * 1993-12-07 1995-06-15 The Procter & Gamble Company Detergent composition containing amine oxide surfactant in the form of agglomerates
US5560858A (en) * 1992-07-15 1996-10-01 The Procter & Gamble Company Dye transfer inhibiting compositions containing a metallocatalyst, a bleach and polyamine N-oxide polymer
US20070031370A1 (en) * 2005-08-04 2007-02-08 Carr Richard V Amine N-oxide based surfactants
US20080098614A1 (en) * 2006-10-03 2008-05-01 Wyeth Lyophilization methods and apparatuses

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL56176A (en) * 1978-01-30 1982-03-31 American Cyanamid Co Process for preparing n-ethylethylenediamine
DE3145735A1 (de) * 1981-11-19 1983-05-26 Hoechst Ag, 6230 Frankfurt Triamin-trioxide, verfahren zu deren herstellung unddiese enthaltende reinigungsmittel

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2169976A (en) * 1934-01-26 1939-08-15 Ig Farbenindustrie Ag Process of producing assistants in the textile and related industries
US2999068A (en) * 1959-04-27 1961-09-05 Procter & Gamble Personal use detergent lotion
US3001945A (en) * 1959-04-29 1961-09-26 Procter & Gamble Liquid detergent composition
US3047579A (en) * 1958-07-18 1962-07-31 Shell Oil Co Process for preparing n-oxides
US3085982A (en) * 1959-04-22 1963-04-16 Procter & Gamble Liquid detergent composition
US3086943A (en) * 1959-06-10 1963-04-23 Procter & Gamble Shampoo containing amine oxide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2169976A (en) * 1934-01-26 1939-08-15 Ig Farbenindustrie Ag Process of producing assistants in the textile and related industries
US3047579A (en) * 1958-07-18 1962-07-31 Shell Oil Co Process for preparing n-oxides
US3085982A (en) * 1959-04-22 1963-04-16 Procter & Gamble Liquid detergent composition
US2999068A (en) * 1959-04-27 1961-09-05 Procter & Gamble Personal use detergent lotion
US3001945A (en) * 1959-04-29 1961-09-26 Procter & Gamble Liquid detergent composition
US3086943A (en) * 1959-06-10 1963-04-23 Procter & Gamble Shampoo containing amine oxide

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2215371A1 (de) * 1971-04-02 1972-10-19 Unilever N.V., Rotterdam (Niederlande) Waschmittel
EP0042188A1 (en) * 1980-06-17 1981-12-23 THE PROCTER & GAMBLE COMPANY Detergent composition containing low levels of amine oxides
US4391726A (en) * 1980-11-28 1983-07-05 The Procter & Gamble Company Detergent composition containing low levels of amine oxides
US4470923A (en) * 1980-11-28 1984-09-11 The Procter & Gamble Company Detergent composition containing low levels of amine oxides
US4588522A (en) * 1982-04-24 1986-05-13 Hoechst Aktiengesellschaft Betaine-amine oxides, a process for their preparation and their use as surfactants
US5560858A (en) * 1992-07-15 1996-10-01 The Procter & Gamble Company Dye transfer inhibiting compositions containing a metallocatalyst, a bleach and polyamine N-oxide polymer
WO1995016016A1 (en) * 1993-12-07 1995-06-15 The Procter & Gamble Company Detergent composition containing amine oxide surfactant in the form of agglomerates
US20070031370A1 (en) * 2005-08-04 2007-02-08 Carr Richard V Amine N-oxide based surfactants
US20080098614A1 (en) * 2006-10-03 2008-05-01 Wyeth Lyophilization methods and apparatuses

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FR1347955A (fr) 1964-01-04
GB1007343A (en) 1965-10-13
NL286808A (is")

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