WO2001010991A1 - Compositions tensioactives aqueuses de sels d'esters de monoalkyl-phosphate et de tensio-actifs amphoteres - Google Patents

Compositions tensioactives aqueuses de sels d'esters de monoalkyl-phosphate et de tensio-actifs amphoteres Download PDF

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Publication number
WO2001010991A1
WO2001010991A1 PCT/US2000/020945 US0020945W WO0110991A1 WO 2001010991 A1 WO2001010991 A1 WO 2001010991A1 US 0020945 W US0020945 W US 0020945W WO 0110991 A1 WO0110991 A1 WO 0110991A1
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WO
WIPO (PCT)
Prior art keywords
aqueous surfactant
surfactant composition
salts
phosphate ester
alkyl
Prior art date
Application number
PCT/US2000/020945
Other languages
English (en)
Inventor
Phillip Loraine Cotrell
Alvino Gabbianelli
Robert Lee Reierson
Original Assignee
Rhodia Inc.
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 Rhodia Inc. filed Critical Rhodia Inc.
Priority to EP00953776A priority Critical patent/EP1204733A1/fr
Priority to AU66171/00A priority patent/AU6617100A/en
Publication of WO2001010991A1 publication Critical patent/WO2001010991A1/fr

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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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • 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
    • C11D1/34—Derivatives of acids of phosphorus
    • C11D1/345—Phosphates or phosphites

Definitions

  • This invention relates to novel aqueous surfactant compositions, particularly to surfactant compositions of alkyl phosphate ester salts and amphoteric surfactants. More particularly, this invention relates to essentially non-irritating aqueous surfactant compositions containing alkyl phosphate ester salts having a high monoalkyl phosphate content and amphoteric surfactants.
  • surfactants and mixtures of surfactants are known for many industrial, commercial and domestic applications. In these uses, there is often a need for the surfactant to be in a pumpable or fluid form for addition to formulations requiring the surfactant since such form enables one to save costs in handling and storing of the composition, as well as ease and convenience in formulating products therewith. Additionally, for numerous reasons, such as formulation flexibility, transportation and storage costs, it is desirable for the surfactant to be available in such pumpable compositions in as high a concentration or proportion of surfactant or active ingredient as possible.
  • novel aqueous surfactant compositions of this invention consist essentially of alkyl phosphate ester salts high in monoalkyl phosphate content and an amphoteric surfactant, wherein said composition is essentially free of compounds having a tetra-alkyl ammonium moiety.
  • This invention also provides aqueous compositions which are comprised of an alkyl phosphate ester salt surfactant composition in which the monoalkyl phosphate (1) and dialkyl phosphate (2) are present in a molar ratio of equal to or greater than 50:50, and an amphoteric surfactant.
  • the amphoteric surfactants useful in this invention do not contain a tetra-alkyl ammonium moiety.
  • Alkyl phosphate ester salts is meant to include alkylether phosphate ester salts (i.e. polyoxyalkylene derivatives of the alkanol(s) from which they are derived) as well as non-alkoxylated derivatives.
  • alkyl phosphate ester salts are mixtures of compounds having the formula (1) and (2):
  • Ri and R 2 are individually C 8 -C 22 linear or branched saturated or unsaturated hydrocarbons, m and n are individually integers from 2 to 4, w, x, y and z are individually integers from 0 to 20 and M is individually hydrogen, an alkali metal, amine or alkanolamine.
  • Figs. 1 to 5 are graphs of dermal irritation scores of compositions of this invention and for comparative compositions.
  • compositions are especially useful in cosmetic and personal care products because of the non-irritating properties of the blend.
  • the aqueous surfactant compositions are preferably essentially free of betaine surfactants, sultaine surfactants, cocoamphodiacetates and cocoamphodipropionates.
  • One of the components is an alkyl phosphate ester that is preferably in the form of a high solids, yet pumpable aqueous composition.
  • Pumpable aqueous surfactant compositions which are particularly useful in this invention are characterized by a low level of residual phosphoric acid and residual alcohol.
  • Pumpable aqueous surfactant compositions of this invention are produced from alkyl phosphate ester compositions high in monoalkyl phosphates relative to dialkyl phosphates, i.e., a molar ratio of mono- to di- alkyl phosphate esters of equal to or greater than 50:50, preferably 80:20 or greater and more preferably greater than 90:10.
  • phosphate ester compositions of low residual phosphoric acid and residual alcohol content and high in monoalkyl phosphates used to produce the aqueous pumpable surfactant composition of this invention are produced by the process disclosed in US Patents 5,463,101 , 5,550,274 and 5,554,781 , as well as in EP Patent publication number EP 0 675,076 A2, especially as described in Example 18 of the EP publication
  • the alkyl phosphate ester salts are prepared by stirring the appropriate alkyl phosphate esters, high in monoalkyl phosphate ester content, into a solution of an appropriate base
  • suitable base materials for producing the salts of the alkyl phosphate esters there may be mentioned sodium, potassium, lithium, or ammonium hydroxides and amines, such as for example, triethanolamine (TEA) and 2- am ⁇ no-2-methyl-1-propanol (AMP) and the like
  • TAA triethanolamine
  • AMP 2- am ⁇ no-2-methyl-1-propanol
  • the salts of the monoalkyl phosphate esters may be of any suitable base acid molar ratio salts, such as 0 8, 1 , 1 5, 1 7 salts and the like
  • Alkyl phosphate esters employed in forming the pumpable aqueous surfactant compositions of this invention are preferably produced from alcohols or mixtures of alcohols typically found in natural oils, for example, coconut oils or rapeseed, carbon chain length of about C 8 to C 22 and/or their alkylene oxide derivatives prepared by reaction with ethylene oxide, propylene oxide or both, randomly or in blocked segments
  • Blends of linear and branched, saturated and unsaturated alcohols and their alkoxylates are permissable but at least about 50% by weight, more preferably at least about 70% by weight, and most preferably, at least about 90% by weight, of the blend should be alcohols having 12 or fewer carbon atom chains
  • the alkyl phosphate ester salts comprise salts of predominately C 10 to C- ⁇ 2 alcohols or C 8 to C 16 alcohols
  • Pumpable aqueous surfactant compositions of this invention have a mono- to di- alkyl phosphate molar ratio of at least 50 50 but preferably equal to or greater than 80 20 for applications requiring greater foaming and detergency and have a solids content of about 20% by weight or more and exhibit one or more pumpable regions over a range of pH values for the aqueous surfactant composition, especially over the pH range of from about pH 5 to about pH 10
  • the pumpable compositions could be, for example, in a lamellar or micellar phase
  • the residual phosphoric acid or residual alcohol content of the pumpable aqueous surfactant compositions of this invention will generally be less than 8% by weight, preferably less than 6% by weight, and more preferably less than 5% by weight of each residual component
  • Higher phosphoric acid content contributes to higher viscosity and salt content and the alcohols, having lower solubility in water, tend to separate or contribute haze to the solution
  • those pumpable aqueous surfactant compositions of this invention which are essentially transparent, more particularly are essentially clear, and even more preferably are essentially colorless when in their pumpable regions
  • Pumpable aqueous surfactant compositions of this invention are characterized by being pumpable or flowable at low temperatures, for example, at temperatures of below 40°C, especially in the range of temperatures of from about 5°C to about 40°C
  • the total solids content of the pumpable aqueous surfactant composition is at least about 20% by weight, it will generally be from about 40% to about 70% by weight alkyl phosphate ester salt
  • amphoteric surfactants useful in the present invention include the imidazo ne-based and fatty amine-based surfactants
  • examples include the imidazoline based amphoteric surfactants such as cocoamidoalkylamino monoacetate (available from Rhodia Inc , as Miranol Ultra C-37)and cocoamidoalkylamino monopropionate (available from Rhodia Inc , as Miranol Ultra CM-SF), sodium cocoamidoalkylamino hydroxypropyl sulfonate (available from Rhodia Inc , as Miranol CS), and sodium caprylamidoalkylamino hydroxypropyl sulfonate (available from Rhodia Inc , as Miranol JS), and the fatty alkyl amine-based amphoteric surfactants such as cocoalkylamine acetates, cocoalkylamine diacetates, cocoalkylamine propionates, cocoalkylamine dipropionates, and coco
  • amphoteric surfactants are the those described in U S Patent
  • Those surfactants are imidazohne-based amphoteric surfactants of high purity and which contain essentially negligible amounts of unalkylated amidoamines, lower amounts of glycolic acid salts, and monchloroacetate salts
  • compositions of the present invention are made by blending alkyl phosphate ester salts high in monoalkyl phosphate content and amphoteric surfactants
  • the blends will typically have a total solids content of from about 5% to about 40% with a ratio of active phosphate ester surfactant to active amphoteric surfactant of from about 100 1 to about 1 100, more typically from about 10 1 to about 1 10, and even more typically from about 3 1 to about 1 3
  • phosphate esters were prepared by phosphation of the selected alcohol or blend of alcohols in accordance with the processes described in European Patent publication EP 0 675,076 A2, particularly Example 18 thereof, with adjustment of reagent charges as appropriate for different alcohol molecular weights or intended ester product distributions
  • a pre-dned reactor was charged, under essentially anhydrous conditions of a dry nitrogen blanket, with 343 5 lb dodecanol which was heated to 35°C to melt and provide an easily stirrable liquid.
  • Polyphosphoric acid (115%), 111.3 lb., was then added to the stirred liquor with cooling to maintain the temperature below 45°C. Stirring was continued for 30 min. to assure a homogenous solution.
  • Phosphoric anhydride powder, 40.0 lb. was then added with cooling to maintain the temperature under 55°C and the rapidly stirred mixture was heated to 80°C and held at that temperature. Reaction progress was followed by the change in the second acid value and, after it had stabilized, 2.5 lb.
  • the product composition determined by 31 P, 13 C and 1 H nuclear magnetic resonance spectroscopy, was, by weight, 6.2% phosphoric acid, 76.0% mono(dodecyl) phosphate, 12.4% di(dodecyl) phosphate, 4.8% nonionics (residual alcohol) and 0.6% water (Karl-Fischer titration). Acid value 1 (first titration inflection point, pH ⁇ 5.6) was 210.7 mg KOH/g sample.
  • the tested solutions were at a total surfactant actives content of 0.5% by weight.
  • the ratio shown in the Summary Table below is the weight ratio of surfactant actives to surfactant actives.
  • SLES-2 sodium lauryl ether sulphate (2 mol EO)
  • Betaine cocoamidopropyl betaine (Bet C-30)
  • UM-140 a mixture of sodium cocoyl isethionate, sodium lauroamphoacetate and sodium methyl cocyl taurate surfactants.
  • SLS Sodium lauryl sulphate @ 0.5% aqueous.
  • the objective of this study was to determine the comparative dermal irritation potential of a series of nine (9) test articles on twenty-five (25) subjects using a 14-Day Cumulative Irritation Assay.
  • the subjects chosen were dependable and able to read and understand instructions. The subjects did not exhibit any physical or dermatological condition that would have precluded application of the test articles.
  • test article A sufficient amount of each test article (approximately 0.2 ml) was placed onto a Parke-Davis Readi-Bandage® occlusive patch, which was applied to the back of each subject between the scapulae and waist, adjacent to the spinal mid-line. All patch preparations and evaluations were made by trained, experienced technicians under the supervision of the Study Director.
  • the highest Total cumulative irritation score that could be obtained equals 924 (22 subjects x 14 days x "3" [highest obtainable irritation score for any of the test articles])
  • the highest possible Mean cumulative irritation score that could be obtained equals 42 (924 - 22 subjects)
  • Test Article #4 The fourteen day human cumulative irritation study conducted with eight surfactants, showed that none of the surfactants were as irritating as sodium lauryl sulfate Test Articles #1 and #2 were the least irritating Almost a 4-fold greater cumulative irritation response was observed with the test articles (#3-8) when compared to Test Articles #1 and 2 Test Article #4 was associated with the greatest irritation Table A summarizes the total cumulative irritancy scores, the mean cumulative irritation scores and ranks the test articles, based on mean cumulative irritancy.
  • test articles by irritancy, from least to most irritating, (based upon the mean cumulative irritancy response) is
  • anionic surfactants the various salt forms (sodium, potassium, amine, etc ) of monoalkyl and monoalkyl ether phosphate esters are inherently mild to the skin and eyes as individual surfactants (Fig 2) Based on traditional thinking, therefore, it would be expected that these compounds when combined with other irritating anionic surfactants such as sodium lauryl sulfate, sodium laureth sulfate, etc , should function as irritation diluents thus reducing the overall system irritation proportional to their use concentration ratios In addition it would be expected that these compounds would act in a similar manner as other common anionic surfactants and react synergistically with recognized irritation mollifying agents such as imidazoline derived amphote ⁇ cs alkyl betaines, alkylamidopropyl betaine, etc , to reduce the overall system irritation

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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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions tensioactives aqueuses de sels d'esters d'alkyl-phosphate dont le rapport molaire entre esters de monoalkyl-phosphate et esters de dialkyl-phosphate est supérieur ou égal à 80:20, ainsi que des tensioactifs amphotères sensiblement exempts de fractions tétra-alkyl-ammonium. Ces compositions tensioactives aqueuses sont très peu irritantes pour la peau.
PCT/US2000/020945 1999-08-05 2000-08-01 Compositions tensioactives aqueuses de sels d'esters de monoalkyl-phosphate et de tensio-actifs amphoteres WO2001010991A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP00953776A EP1204733A1 (fr) 1999-08-05 2000-08-01 Compositions tensioactives aqueuses de sels d'esters de monoalkyl-phosphate et de tensio-actifs amphoteres
AU66171/00A AU6617100A (en) 1999-08-05 2000-08-01 Aqueous surfactant compositions of monoalkyl phosphate ester salts and amphoteric surfactants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14745399P 1999-08-05 1999-08-05
US60/147,453 1999-08-05

Publications (1)

Publication Number Publication Date
WO2001010991A1 true WO2001010991A1 (fr) 2001-02-15

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EP (1) EP1204733A1 (fr)
AU (1) AU6617100A (fr)
WO (1) WO2001010991A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6821944B2 (en) 2001-06-04 2004-11-23 Rhodia, Inc. Compositions of alkanolamine salts of alkyl phosphate esters
US6855677B1 (en) * 1999-10-12 2005-02-15 Kao Corporation Detergent composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4132679A (en) * 1976-08-24 1979-01-02 Kao Soap Co., Ltd. Low irritant shampoo composition
EP0224796A2 (fr) * 1985-11-28 1987-06-10 Kao Corporation Composition détergente
WO1998020093A2 (fr) * 1996-11-05 1998-05-14 Kao Corporation Compositions aqueuses concentrees d'un tensioactif de type betaine et leur procede de preparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4132679A (en) * 1976-08-24 1979-01-02 Kao Soap Co., Ltd. Low irritant shampoo composition
EP0224796A2 (fr) * 1985-11-28 1987-06-10 Kao Corporation Composition détergente
WO1998020093A2 (fr) * 1996-11-05 1998-05-14 Kao Corporation Compositions aqueuses concentrees d'un tensioactif de type betaine et leur procede de preparation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6855677B1 (en) * 1999-10-12 2005-02-15 Kao Corporation Detergent composition
US7504370B2 (en) 1999-10-12 2009-03-17 Kao Corporation Detergent composition
US6821944B2 (en) 2001-06-04 2004-11-23 Rhodia, Inc. Compositions of alkanolamine salts of alkyl phosphate esters

Also Published As

Publication number Publication date
EP1204733A1 (fr) 2002-05-15
AU6617100A (en) 2001-03-05

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