EP0988368A1 - Procede de fabrication d'une composition tensio-active solide a base d'oxyde d'amine - Google Patents

Procede de fabrication d'une composition tensio-active solide a base d'oxyde d'amine

Info

Publication number
EP0988368A1
EP0988368A1 EP97926875A EP97926875A EP0988368A1 EP 0988368 A1 EP0988368 A1 EP 0988368A1 EP 97926875 A EP97926875 A EP 97926875A EP 97926875 A EP97926875 A EP 97926875A EP 0988368 A1 EP0988368 A1 EP 0988368A1
Authority
EP
European Patent Office
Prior art keywords
acid
amine oxide
complexing
carbon atoms
groups
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.)
Withdrawn
Application number
EP97926875A
Other languages
German (de)
English (en)
Inventor
Isauro Manuel E. Misajon
Pamela Carlos Angeles
Robert Henry Callicott
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
Original Assignee
Procter and Gamble 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
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP0988368A1 publication Critical patent/EP0988368A1/fr
Withdrawn legal-status Critical Current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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates
    • 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
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2082—Polycarboxylic acids-salts thereof
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • 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
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/361—Phosphonates, phosphinates or phosphonites
    • 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
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/364—Organic compounds containing phosphorus 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C11D3/3761—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in solid compositions

Definitions

  • the present invention relates to a process for preparing solid compositions containing amine oxide-acid salts.
  • Such compositions are a source of solid, concentrated amine oxide surfactants for incorporation into cleaning products, especially solid or granular cleaning products.
  • Amine oxides are commonly used in cleaning compositions to boost and maintain suds formation.
  • Such compositions include, for example, laundry, shampoo and dish washing detergent compositions.
  • amine oxide surfactants from the corresponding tertiary amine are known. Such methods involve the conversion of a tertiary amine in the presence of a strong oxidizing agent to the corresponding amine oxide. For example, tertiary amines can be reacted with hydrogen peroxide to yield a 30-40% aqueous solution of the corresponding amine oxide. Catalysts are commonly used to facilitate the reaction. Most of these methods, however, result in liquid formulations containing the amine oxide.
  • solid amine oxide surfactant formulations are desirable than typical amine oxide surfactant formulations that are commercially available, such as in liquid, gel, or paste form.
  • amine oxide surfactants have been many attempts at preparing amine oxide surfactants in solid or granular formulations.
  • U.S. 5,399,296, granted on March 21, 1995 to Wierenga et al. and U.S. 5,389,306 granted on February 14, 1995 to Wierenga et al. disclose solid amine oxide compositions containing amine oxide-maleic acid salts and the process for making such compositions.
  • the foregoing considerations involving amine oxide surfactant formulations and the processes for preparing them indicate that there is a continuing need to provide solid formulations containing amine oxide surfactants. None of the existing art provides all of the advantages and benefits of the present invention.
  • solid amine oxide compositions containing amine oxide-maleic acid salts can be formed.
  • Such other solid amine oxide surfactant compositions can be used as a source of amine oxide surfactants in cleaning compositions.
  • the present invention is directed to a process for preparing solid amine oxide surfactant compositions which are useful in formulating detergent products, such as laundry detergents, shampoos, personal cleansing compositions, and cosmetic compositions, especially solid or granular cleaning products.
  • the process comprises admixing the complexing acid with an amine oxide surfactant formulation by admixing 1 mole of complexing acid with X mole(s) of amine oxide, where X is from about 1 to about equal to the number of acid groups of the complexing acid.
  • the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed.
  • the formed precipitate is separated from the admixture, preferably by mechanical means, and allowed to dry.
  • the separated precipitate forms the solid compositions of the present invention, which solid compositions consist of the amine oxide and complexing acid described above.
  • solid compositions mean particulate (e.g. powders, granules, agglomerates) and non-particulate solids. As used herein, all pKa and pH values are measured in water at 25°C.
  • Amine oxide formulations for use in the process herein comprise varying amounts of amine oxide surfactant therein.
  • Such amine oxide formulations, and the processes for preparing them, are well known in the surfactant art.
  • the amine oxide formulations for use in the instant process comprise varying percentages of amine oxide surfactant.
  • Amine oxide surfactants are commercially available in many physical forms, including liquid, paste, gel and solid.
  • the percentage of amine oxide surfactant in the formulation, as well as the type of such amine oxide surfactant, are not critical to the successful operation of the instant process. Accordingly, any known or conventional amine oxide formulation can be used.
  • Such known or conventional formulations typically contain from about 3% to about 80%, more typically from about 5% to about 20%, most preferably from about 5% to about 10% by weight of amine oxide surfactant in a dilute water solution. It is understood, however, that formulations containing higher and lower concentrations of amine oxide surfactant can also be used in the instant process.
  • Amine oxide surfactants for use in the instant process preferably have the formula RR'R"NO, where R is a substituted or unsubstituted alkyl or alkenyl group containing from about 6 to about 30, preferably about 8 to 18 carbon atoms.
  • Groups R' and R" are each substituted or unsubstituted alkyl or alkenyl groups containing from about 1 to about 18, preferably from about 1 to about 4, carbon atoms.
  • R' and R" are each methyl groups, examples of which include dodecyldimethyl amine oxide, tetradecyldimethyl amine oxide, hexadecyldimethyl amine oxide, octadecyldimethyl amine oxide, and coconutalkyldimethylamine oxides.
  • Suitable amine oxide surfactants for use in the instant process include, but are not limited to, dodecyldimethyl amine oxide, tridecyldimethyl amine oxide, tetradecyldi-methyl amine oxide, pentadecyldimethyl amine oxide, hexadecyldimethyl amine oxide, heptadecyldimethyl amine oxide, octadecyldimethyl amine oxide, dodecyldiethyl amine oxide, tetradecyldimethyl amine oxide, hexadecyldiethyl amine oxide, octadecyldiethyl amine oxide, dodecyldipropyl amine oxide, tetradecyldipropyl amine oxide, hexadecyldipropyl amine oxide, octadecyldipropyl amine oxide, dodecyldibut
  • ADMOXTM is a C14 amine oxide dihydrate.
  • ADMOXTM and other amine oxides useful in the present process are set forth in U.S. Patent No. 5,292,955 (Smith and Sauer, issued March 8, 1994).
  • amine oxide surfactants made by the oxidation of tertiary amines prepared from mixed alcohols obtainable from coconut oil. Such coconutalkyl amine oxides are preferred from an economic standpoint inasmuch as it is not necessary for the present purposes, to separate the mixed alcohol fractions into their pure components to secure the pure chain length fractions of the amine oxides.
  • Amine oxide formulations for use in the present process can be prepared by known and conventional methods. Such methods normally involve the controlled oxidation of tertiary amines to the corresponding amine oxide using a strong oxidizing agent.
  • a preferred oxidizing agent is hydrogen peroxide.
  • a dilute, or preferably concentrated (30% by weight of more), hydrogen peroxide solution is added in a stoichiometric or greater amount to a liquid solution containing the tertiary amine for conversion thereof to the amine oxide.
  • Reaction rates and amine oxide yields can be improved by incorporation of catalysts and or chelating agents well known in the surfactant art for this particular application. Methods for making amine oxide surfactants are described, for example, in U.S.
  • Patent 3,215,741 Chadwick, issued November 2, 1965
  • U.S. Patent 3,223,647 Drew and Voss, issued December 14, 1965
  • British Patent 437,566 issued October 31, 1935
  • U.S. Patent 4,565,891 Correa and Riley, issued July 19, 1984.
  • the process for preparing the solid compositions of the present invention involved admixing a complexing acid with the amine oxide formulation described herein before.
  • Complexing acid is defined as a saturated carboxylic acid with at least 5 carbon atoms, unsaturated carboxylic acid with at least 5 carbon atoms, phosphonic acid, and mixtures thereof.
  • Such complexing acids will effectively precipitate amine oxide surfactants from the amine oxide formulations.
  • carboxylates means carboxyl-containing compounds generally.
  • the complexing acids of the present invention can be in a powdery form, or in an aqueous solution, although the physical form of the complexing acid is not critical to the invention.
  • the complexing acid is soluble in water at less than about 35°C.
  • E ⁇ xamples of saturated and unsaturated carboxylic acids with at least 5 carbon atoms includes citric acid, polyacrylic acid, malonic acid, adipic acid, oxalic acid, glutaric acid, pthalic acid, lauric acid, oleic acid, benzoic acid, and butyric acid.
  • phosphonic acids examples include tetra sodium pyrophosphate (TSPP), sodium tripolyphosphate (STPP), diethylene triamine penta methyl phosphonic acid, hydroxyethane diphosphonic acid, and ethylenediamine tetra methylene phosphonic acid.
  • TSPP tetra sodium pyrophosphate
  • STPP sodium tripolyphosphate
  • diethylene triamine penta methyl phosphonic acid hydroxyethane diphosphonic acid
  • hydroxyethane diphosphonic acid hydroxyethane diphosphonic acid
  • ethylenediamine tetra methylene phosphonic acid examples include ethylenediamine tetra methylene phosphonic acid.
  • Preferred polyacrylic acids have a molecular weight range of from about 2,500 to 70,000, preferably a molecular weight range of from about 10,000 to about 50,000.
  • Water soluble salts of the complexing acid can also be used in the instant process.
  • Such salts can comprise alkali metals (e.g., sodium, potassium), alkali earth metals, ammonium, substituted ammonium, and so forth.
  • alkali metals e.g., sodium, potassium
  • alkali earth metals e.g., sodium, potassium
  • ammonium substituted ammonium
  • Preferred among such salts are sodium citrate, diammonium citrate, sodium tripolyphosphate and sodium pyrophosphate.
  • Other water soluble salts can be used in the instant process provided that such salts are compatible with the amine oxide surfactant selected for use herein.
  • An essential step in the instant process is adding the complexing acid in the requisite amounts to the amine oxide formulation to form a solid amine oxide surfactant composition. It is preferred that the amine oxide be diluted in a water solution, having an active level of from about 3% to about 80%, preferably from about 5% to about 20%, most preferably from about 5% to about 10%. pH adjustment of the amine oxide formulation to the requisite level to about 1 to about 3 is normally needed when the complexing acid is used in the instant process. Precipitation of the desired amine oxide salt will not occur to any large extent until such admixture pH values are realized.
  • the complex is formed by admixing 1 mole of complexing acid with X mole(s) of amine oxide, where X is from about 1 to about equal to the number of acid groups of the complexing acid. X should be within about plus or minus 25%, preferably about plus or minus 10%, of the number of acid groups in the complexing acid.
  • the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed. The formed precipitate is separated from the admixture, preferably by mechanical means, and allowed to dry.
  • the process of the present invention is described herein in terms of the addition of the complexing acid to an amine oxide formulation. It is understood, however, that any reference herein to complexing acid implicitly includes salts of complexing acids (described herein before), complexing acids which are acids, and mixtures thereof. Process
  • the process of the present invention comprises admixing the complexing acid and an amine oxide formulation to form a visible precipitate therein, and then separating the formed precipitate from the admixture.
  • the process is described in detail as follows.
  • one mole of a complexing acid and X moles of an amine oxide formulation described herein (10% active in a dilute solution of water) are admixed, wherein X is from about 1 to about equal to the number of acid groups of the complexing acid.
  • the pH of the admixture is from about 1 to about 3, whereby a visible precipitate in the admixture is formed.
  • the formed precipitate made in accordance with the instant process is a salt of the amine oxide surfactant and complexing acid.
  • an excess of complexing acid is used to accelerate the formation of the precipitate.
  • An excess of about 30% complexing acid above the molar amount described above is preferred.
  • the formed precipitate is separated from the admixture.
  • separation is accomplished by mechanical means such as screening, filtering, centrifuging and the like.
  • the separated precipitate can then be washed with cold water (pH adjusted to about the pKa of the amine oxide) to remove unprecipitated reactants, and then dried to form a solid formulation.
  • the solid formulation can be reduced to fine particles, agglomerated, and so forth. Since the precipitate can be separated by mechanical means, there is no need to use organic extraction solvents to perform such separations.
  • citric acid complexing acid is admixed with about 30 grams of amine oxide solution (C14 alkyldimethyl amine oxide, 10% active in a solution of water).
  • the molar ratio of complexing acid to active amine oxide is about 1 :2.
  • the pH of the admixture of amine oxide solution and citric acid is from about 1 to about 3. pH is adjusted with the addition of excess citric acid. A visible precipitate forms almost immediately.
  • the admixture is allowed to set for about 5 minutes.
  • the precipitate is then filtered from the admixture, washed with water (pH of 7), in which the water has substantially all the impurities removed, and air dried before it is reduced to a fine powder.
  • the citric acid is preferably in a powder form.
  • Example 2 The process described in Example 1 is repeated, except that 30 grams of C16 alkyldimethyl amine oxide (7.85% solution) is admixed with a solution of 0.76 grams of citric acid, thereby forming a precipitate. After adding the initial citric acid and after the precipitate is formed, an additional 0.40 grams of citric acid is added to adjust the viscosity. The molar ratio of complexing acid to active amine oxide is 1:1.5.
  • Example 2 The process described in Example 1 is repeated, except that 5.27 grams of C16 alkyldimethyl amine oxide (6.4% solution) is admixed with a solution of
  • citric acid 0.09 grams of citric acid.
  • the molar ratio of complexing acid to active amine oxide is 1:3, and the pH of C16 alkyldimethyl amine oxide solution is adjusted using 1 N HCI to a pH of 0.97, before the addition of the citric acid.
  • Example 4 The process described in Example 1 is repeated except that 365 grams of
  • C14 alkyldimethyl amine oxide (10% solution) is admixed with 4.31 grams of diethylene triamine penta methyl phosphonic acid (25% active).
  • the molar ratio of complexing acid to active amine oxide is 1:5, and the pH is adjusted using 1N HCI to a pH of 1.0 before the addition of the complexing acid.
  • Example 6 The process described in E ⁇ xample 1 is repeated except that 47 grams of C14 alkyldimethyl amine oxide (9.8% solution) is admixed with 9.35 grams of polyacrylic acid (molecular weight 4,500) complexing acid (48% active). The molar ratio of complexing acid to active amine oxide is 1 :24. No pH adjustment is necessary before the addition of the polyacrylic acid.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des compositions solides à base d'oxyde d'amine, pouvant servir à élaborer des produits détergents tels que des détergents à lessive, des shampooings, des compositions pour l'hygiène personnelle et des compositions cosmétiques, en particulier des produits de nettoyage solides ou granulaires. Ces compositions solides sont constituées (a) d'oxyde d'amine et (b) d'acide complexant. L'acide complexant est défini comme un acide carboxylique saturé ou insaturé avec au moins 5 atomes de carbone, un acide phosphonique et leurs mélanges.
EP97926875A 1997-06-03 1997-06-03 Procede de fabrication d'une composition tensio-active solide a base d'oxyde d'amine Withdrawn EP0988368A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1997/009510 WO1998055580A1 (fr) 1997-06-03 1997-06-03 Procede de fabrication d'une composition tensio-active solide a base d'oxyde d'amine

Publications (1)

Publication Number Publication Date
EP0988368A1 true EP0988368A1 (fr) 2000-03-29

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ID=22261008

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97926875A Withdrawn EP0988368A1 (fr) 1997-06-03 1997-06-03 Procede de fabrication d'une composition tensio-active solide a base d'oxyde d'amine

Country Status (5)

Country Link
EP (1) EP0988368A1 (fr)
AR (1) AR015846A1 (fr)
AU (1) AU3153497A (fr)
CA (1) CA2293527A1 (fr)
WO (1) WO1998055580A1 (fr)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA797200A (en) * 1964-05-25 1968-10-22 E. Davis Jerry Detergent compositions
US4359413A (en) * 1981-03-17 1982-11-16 The Procter & Gamble Company Solid detergent compositions containing alpha-amine oxide surfactants
CA2025973A1 (fr) * 1989-10-02 1991-04-03 Albemarle Corporation Detergent a lessive surpuissant
US5292955A (en) * 1991-07-26 1994-03-08 Ethyl Corporation Amine oxide complexes
US5399296A (en) * 1994-04-22 1995-03-21 The Procter & Gamble Company Solid compositions containing amine oxide-maleic acid salts
US5389306A (en) * 1994-04-22 1995-02-14 The Procter & Gamble Company Process for making solid formulations containing amine oxide surfactants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9855580A1 *

Also Published As

Publication number Publication date
WO1998055580A1 (fr) 1998-12-10
CA2293527A1 (fr) 1998-12-10
AR015846A1 (es) 2001-05-30
AU3153497A (en) 1998-12-21

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