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WO1996029977A1 - Compositions based on apg and at least one additional nonionic sugar cosurfactant - Google Patents

Compositions based on apg and at least one additional nonionic sugar cosurfactant Download PDF

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Publication number
WO1996029977A1
WO1996029977A1 PCT/US1996/003643 US9603643W WO9629977A1 WO 1996029977 A1 WO1996029977 A1 WO 1996029977A1 US 9603643 W US9603643 W US 9603643W WO 9629977 A1 WO9629977 A1 WO 9629977A1
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WIPO (PCT)
Prior art keywords
cosurfactant
composition according
fatty acid
acid amide
polyhydroxy fatty
Prior art date
Application number
PCT/US1996/003643
Other languages
French (fr)
Inventor
John Frederick Hessel
Original Assignee
Henkel Corporation
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 Henkel Corporation filed Critical Henkel Corporation
Priority to EP96910463A priority Critical patent/EP0817605A4/en
Priority to AU53650/96A priority patent/AU5365096A/en
Priority to BR9607946A priority patent/BR9607946A/en
Publication of WO1996029977A1 publication Critical patent/WO1996029977A1/en
Priority to MXPA/A/1997/007233A priority patent/MXPA97007233A/en

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    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/38—Gaseous or foamed well-drilling compositions
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to alkyl polyglycoside compositions which comprise one or more nonionic sugar cosurfactants.
  • compositions comprising:
  • R 1 is a monovalent organic radical having from about 6 to about 30 carbon atoms;
  • R 1 is divalent alkylene radical having from 2 to 4 carbon atoms;
  • Z is a saccharide residue having 5 or 6 carbon atoms;
  • b is a number having a value from 0 to about 12; and
  • a is a number having a value from 1 to about 6;
  • nonionic sugar cosurfactants one or more nonionic sugar cosurfactants; with the proviso that when the nonionic sugar cosurfactant is a polyhydroxy fatty acid amide or an aldobionamide the composition must contain two or more of said sugar cosurfactants; further provided that when the nonionic sugar cosurfactant is a mixture of a polyhydroxy fatty acid amide and an aldobionamide the composition must contain at least one additional sugar cosurfactant; and
  • (c) optionally one or more additional surfactants selected from the group consisting of anionic, zwitterionic, amphoteric, nonionic and cationic surfactants; wherein the weight ratio of (a)+(b):(c) is equal to from about 1:10 to about 10:1; and wherein the weight ratio of (b):(a) is equal to from about 1:3 to 3:1.
  • additional surfactants selected from the group consisting of anionic, zwitterionic, amphoteric, nonionic and cationic surfactants
  • compositions of the invention will be useful in laundry, personal cleaning products, dishwashing, fire fighting, oil well drilling, ore benefication, solution mining, washing hair, and preparation of foamed solid structures applications.
  • the nonionic sugar cosurfactant is selected from the group consisting of alkyl glucose esters, aldobionamides, gluconamides, glyceramides, glyceroglycolipids and polyhydroxy fatty acid amides.
  • alkyl polyglycosides which can be used in the compositions according to the invention have the formula I
  • R 1 is a monovalent organic radical having from about 6 to about 30 carbon atoms
  • R 2 is divalent alkylene radical having from 2 to 4 carbon atoms
  • Z is a saccharide residue having 5 or 6 carbon atoms
  • b is a number having a value from 0 to about 12
  • a is a number having a value from 1 to about 6.
  • Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero.
  • Such alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, or PLANTAREN® surfactants from Henkel Corporation, Ambler, PA., 19002. Examples of such surfactants include but are not limited to:
  • APG® 225 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
  • APG® 425 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.6.
  • APG® 625 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
  • APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
  • GLUCOPON® 600 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
  • PLANTAREN® 2000 Surfactant - a C 8 . 16 alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
  • PLANTAREN® 1300 Surfactant - a C 12-16 alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
  • alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I wherein Z represents a moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is a number having a value from 1 to about 6; b is zero; and R 1 is an alkyl radical having from 8 to 20 carbon atoms.
  • compositions are characterized in that they have increased surfactant properties and an HLB in the range of about 10 to about 16 and a non-Flory distribution of glycosides, which is comprised of a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3.
  • compositions also known as peaked alkyl polyglycosides
  • the relative distribution of the various components, mono- and poly-glycosides, in the resulting product changes and the concentration in the product of the polyglycosides relative to the monoglycoside increases as well as the concentration of individual polyglycosides to the total, i.e. DP2 and DP3 fractions in relation to the sum of all DP fractions.
  • Such compositions are disclosed in U.S. patent 5,266,690, the entire contents of which are incorporated herein by reference.
  • nonionic sugar cosurfactant refers to surfactants that are based on saccharide moieties.
  • Representative examples of such nonionic sugar cosurfactants include, but are not limited thereto, alkyl glucose ester, aldobionamide, gluconamide, glyceramide, glyceroglycolipid and polyhydroxy fatty acid amide surfactants which are described more fully hereinbelow.
  • alkyl glucose ester sugar cosurfactants are generally disclosed in U.S. patent Nos. 5,109,127 and 5,190,747 the entire contents of both of which are incorporated herein by reference. These sugar cosurfactants have the general formula:
  • R represents a fatty acid residue of 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms and R 1 represents an alkyl group having 2 to 6 carbon atoms.
  • alkyl glucose esters are 1-ethyl-6-caprylglucoside, 1-ethyl-6-laurylglucoside, 1-butyl-6- caprylglucoside, 1-ethyl-6-palmitylglucoside and 1-ethyl-6-oleylglucoside.
  • aldobionamide sugar cosurfactants are generally disclosed in U.S. Patent No. 5,310,542 and in published European Patent Application No. 550,281 both of which are incorporated herein by reference.
  • An Aldobionamide is generally defined as the amide of an aldobionic acid or aldobionolactone and an aldobionic acid in turn is defined as a sugar substance (e.g. any cyclic sugar) in which the aldehyde group has been replaced by a carboxylic acid which upon drying is capable of cyclizing to form an aldonolactone.
  • the aldobionamides can be based on compounds comprising two saccharide units, e.g.
  • lactobionamides maltobionamides, cellobionamides, melibionamides, or gentiobionamides, or they can be based on compounds comprising more than two saccharide units provided that the polysaccharide has a terminal sugar unit with an aldehyde group available.
  • the preferred aldobionamides of the present invention are lactobionamides of the formula wherein R 1 and R 2 are the same or different and are selected from hydrogen and an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g. alkyl groups and alkenyl groups which groups may also include a heteroatom such as N, O, S, present, for instance, as an amide, carboxy, ether and/or saccharide moiety) except that R 1 and R 2 cannot simultaneously be hydrogen.
  • the aliphatic hydrocarbon radical preferably contains up to 24 carbon atoms, most preferably from 8 to 18 carbon atoms.
  • lactobionamides are N-propyl lactobionamide, N-pentyl lactobionamide, N-decyl lactobionamide, N-hexadecyl lactobionamide, N-oleyl lactobionamide, N-dodecyl-N-methyl lactobionamide, and N-dodecyloxypropyl lactobionamide.
  • gluconamide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,386 the entire contents of which is incorporated herein by reference. These cosurfactants have the general formula:
  • Representative examples of such cosurfactants areN-octylerythronamide, N-decylerythronamide, N- dodecylerythronamide, N-tetradecylerythronamide, N- decylxylonamide and N-dodecylxylonamide.
  • glyceramide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,387 the entire contents of which is incorporated herein by reference. These cosurfactants have the general formula:
  • R is a C 8 to C 24 straight or branched chained, saturated or unsaturated aliphatic hydrocarbon in which the R group may also be substituted by a heteroatom selected from oxygen, nitrogen and sulfur.
  • Representative examples of such cosurfactants are N-octylglyceramide, N-decylglyceramide and N-hexadecylglyceramide.
  • the glyceroglycolipid sugar cosurfactants are generally disclosed in U.S. Patent 5,358,656, and published European Patent Application No. 550,279 the disclosure of each of which is incorporated herein by reference.
  • the glyceroglycolipids can be of the formula:
  • a 1 -O-CH 2 -CH (B)-CH 2 NRR 1 wherein A 1 is a saccharide, preferably having one or more saccharide units, more preferably a mono or disaccharide and most preferably a monosaccharide such as glucose or galactose; R and R 1 are the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having from 1 to about 24, preferably from about 6 to about 18 carbon atoms; B is OH or a NR 2 R 3 group, wherein R 2 and R 3 may be the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having 1 to 24, preferably from 6 to 18 carbon atoms, and NRR 1 and B are positionally interchangeable.
  • cosurfactants are 3-(butylamino)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(octylamino)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(eicosylamino)-2-hydroxypropyl- ⁇ -D- galactopyranoside, 3- (butylamino)-2-hydroxypropyl- ⁇ -D-glucopyranoside, and 3-(pentylamino)-2-hydroxypropyl- ⁇ -D-mannopyranoside.
  • glyceroglycolipid cosurfactants are disclosed in published European Patent Application No. 550,280 which is incorporated herein by reference. These cosurfactants are of the formula:
  • cosurfactants are 3-(butyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(eicosyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(decyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(butyloxy)-2-hydroxypropyl- ⁇ -D-glucopyranoside, 3-(octyloxy)-2-hydroxypropyl- ⁇ -D-mannopyranoside, 3-(tetradecyloxy)-2-hydroxypropyl- ⁇ -D-lactoside, 3-(octadecyloxy)-2-hydroxypropyl- ⁇ -D-maltoside, 3-(octyloxy)-2-hydroxypropyl- ⁇ -D-galactotrioside, and 3-(dodecyloxy)-2-hydroxypropyl- ⁇ -D-cellotrioside.
  • the polyhydroxy fatty acid amide sugar cosurfactants are generally disclosed in U.S. Patent Nos. 5,174,927, 5,223,179 and 5,332,528 the entire disclosure of each of which is incorporated herein by reference.
  • the polyhydroxy fatty acid amide surfactant component of the present invention comprises compounds of the structural formula: R 2 C(O)N(R 1 )Z wherein : R 1 is H, C 1 -C 4 hydrocarbyl , 2-hydroxy ethyl , 2-hydroxy propyl or a mixture thereof, preferably C 1 -C 4 alkyl, more preferably C 1 or C 2 alkyl, most preferably C 1 alkyl (i.e., methyl); and R 2 is a C 5 -C 31 hydrocarbyl, preferably straight chain C 7 -C 19 alkyl or alkenyl, more preferably straight chain C 6 -C 17 alkyl or alkenyl, most preferably straight chain C 11 -C 17 alkyl or alkenyl, or mixture
  • Z preferably will be derived from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose.
  • high dextrose corn syrup, high fructose corn syrup, and high maltose corn syrup can be utilized as well as the individual sugars listed above. These corn syrups may yield a mix of sugar components for Z. It should be understood that it is by no means intended to exclude other suitable raw materials.
  • Z preferably will be selected from the group consisting of -CH 2 -(CHOH)n-CH 2 OH, -CH(CH 2 OH) -(CHOH) n-1 -CH 2 OH, -CH 2 -(CHOH) 2 (CHOR') (CHOH)-CH 2 OH, where n is an integer from 3 to 5, inclusive, and R' is H or a cyclic or aliphatic monosaccharide, and alkoxylated derivatives thereof. Most preferred are glycityls wherein n is 4, particularly -CH 2 -(CHOH) 4 -CH 2 OH.
  • Formula R 1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
  • R 2 C(O)N ⁇ can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
  • Z can be 1-deoxyglucityl, 2-deoxyfructityl, 1-deoxymaltityl, 1-deoxylactityl, 1-deoxygalactityl, 1-deoxymannityl, 1-deoxymaltotriotityl, etc.
  • cosurfactants are N-methyl-N-1-deoxyglucityl cocoamide and N-methyl-N-1- deoxyglucityl tallowamide.
  • R is a C 7 -C 21 hydrocarbyl species, i.e. coconut, tallow, palm fatty alkyl and oleyl
  • R 1 is a C 1 to C 6 hydrocarbyl or substituted hydrocarbyl species, i.e. N-alkyl-N-(1,2-propanediol) and N-hydroxyalkyl-N-1,2-propane diol fatty acid amides.
  • cosurfactants are the tallow amide of 3-[2- (hydroxyethyl)amino]-1,2-propanediol (HEAPD), the palmitate amide of 3-methylamino-1,2-propanediol (MAPD) and the lauramide of MAPD.
  • Anionic surfactants can be selected from the group consisting of sulfates, sulfonates, carboxylates and mixtures thereof.
  • the surfactants are neutralized with a cationic moiety or moieties selected from the group consisting of alkali metal, e.g. sodium or potassium, alkaline earth metal, e.g. calcium or magnesium, ammonium, substituted ammonium, including mono-, di-, or tri-. ethanolammonium cations. Mixtures of cations can be desirable.
  • the anionic surfactants which may be useful in the present invention all have detergent properties and are all water soluble or dispersible in water.
  • alkylbenzene sulfonate One class of surfactants which may be used in this invention is an alkylbenzene sulfonate.
  • the alkyl group can be either saturated or unsaturated, branched or straight chain and is optionally substituted with a hydroxy group.
  • Middle phenyl positions are generally preferred for volume of foaming in light soil conditions. However, in heavier soil conditions phenyl attachment at the 1- or 2-position is preferred.
  • the preferred alkylbenzene sulfonates contain a straight alkyl chain containing from about 9 to about 25 carbon atoms, preferably from about 10 to about 13 carbon atoms, and the cation is sodium, potassium, ammonium, mono-, di-, or triethanolammonium, calcium or magnesium and mixtures thereof. Magnesium is the preferred cationic moiety. These same cations are preferred for other anionic surfactants and ingredients.
  • the magnesium alkylbenzene sulfonates where the phenyl group is attached near the middle of the alkyl chain are surprisingly better than the ones with the phenyl near the end of the chain when the polysaccharide chain averages greater than about 3 saccharide units.
  • Suitable alkylbenzene sulfonates include C 11 alkylbenzene sulfonates with low 2-phenyl content.
  • surfactants which may be used in this invention are carboxylates, e.g. fatty acid soaps and similar surfactants.
  • the soaps can be saturated or unsaturated and can contain various substituents such as hydroxy groups and alpha-sulfonate groups.
  • the hydrophobic portion of the soap is a straight chain saturated or unsaturated hydrocarbon.
  • the hydrophobic portion of the soap usually contains from about 6 to about 30 carbon atoms, preferably from about 10 to about 18 carbon atoms.
  • the cationic moiety (M) for carboxylate surfactants is selected from the group consisting of alkali metal, for example, sodium or potassium, alkaline earth metal, for example, calcium or magnesium, ammonium, or substituted ammonium, including mono-, di-, or triethanolammonium cations. Mixtures of cations can be desirable.
  • alkyl (paraffin or olefin) sulfonates preferably with a more central hydrophilic group, containing from about 6 to about 30 carbon atoms.
  • alkyl (paraffin or olefin) sulfonates preferably with a more central hydrophilic group, containing from about 6 to about 30 carbon atoms. Examples include C 14-15 paraffin sulfonates and C 14-16 olefin sulfonates.
  • surfactants which contain sulfonate or carboxylate groups can be used in the compositions of the invention.
  • These other surfactants may include, for example, the sulfosuccinate surfactants disclosed in U.S. Patent 5,015,414 the entire contents of which is incorporated herein by reference, and the dialkyl sulfosuccinate surfactants disclosed in U.S. Patent 4,839,098, the entire contents of which is incorporated herein by reference.
  • One group of surfactants that are of interest because of their superior detergency are the zwitterionic surfactants which contain both a cationic group, either ammonium, phosphonium, sulfonium or mixtures thereof and a sulfonate or carboxylate group. Preferably there are at least about four atoms separating the cationic and anionic groups.
  • Suitable zwitterionic surfactants are disclosed in U.S. Pat. Nos. 4,159,277; 3,928,251; 3,925,262; 3,929,678; 3,227,749; 3,539,521; 3,383,321; 3,390,094; and 3,239,560, incorporated herein by reference. Such surfactants are especially desirable for shampoos.
  • amphoteric surfactants which have the same general structure as the zwitterionic surfactants but with an amine group instead of the quaternary ammonium group.
  • Suitable amphoteric surfactants are disclosed, for example, in U.S. Patent 3,929,678, which is incorporated herein by reference.
  • Suitable nonionic detergent surfactants are generally disclosed in U.S. Pat. No. 3,929,678, Laughlin et al., issued Dec. 30, 1975, at column 13, line 14 through column 16, line 6, incorporated herein by reference. Exemplary, non-limiting classes of useful nonionic surfactants are listed below.
  • the polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols are preferred. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 12 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide.
  • the ethylene oxide is present in an amount equal to from about 5 to about 25 moles of ethylene oxide per mole of alkyl phenol.
  • nonionic surfactants of this type include IGEPAL® CO-630, marketed by the GAF Corporation; and TRITON® X-45, X-114, X-100, and X-102, all marketed by the Rohm & Haas Company.
  • This category includes, for example, alkyl phenol alkoxylates such as the alkylphenol ethoxylates.
  • the condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide can either be straight or branched, primary or secondary, and generally contains from about 8 to about 22 carbon atoms. Particularly preferred are the condensation products of alcohols having an alkyl group containing from about 10 to about 20 carbon atoms with from about 2 to about 18 moles of ethylene oxide per mole of alcohol. Examples of commercially available nonionic surfactants of this type include TERGITOL® 15-S-9
  • the hydrophobic portion of these compounds preferably has a molecular weight of from about 1500 to about 1800 and exhibits water insolubility.
  • the addition of polyoxyethylene moieties to this hydrophobic portion tends to increase the water solubility of the molecule as a whole, and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50% of the total weight of the condensation product, which corresponds to condensation with up to about 40 moles of ethylene oxide.
  • Examples of compounds of this type include certain of the commercially-available PLURONIC® surfactants, marketed by BASF.
  • the condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine consist of the reaction product of ethylenediamine and excess propylene oxide, and generally has a molecular weight of from about 2500 to about 3000.
  • This hydrophobic moiety is condensed with ethylene oxide to the extent that the condensation product contains from about 40% to about 80% by weight of polyoxyethylene and has a molecular weight of from about 5,000 to about 11,000.
  • this type of nonionic surfactant include certain of the commercially available TETRONIC® compounds, marketed by BASF.
  • Semi-polar nonionic surfactants are a special category of nonionic surfactants which include water-soluble amine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms.
  • Semi-polar nonionic detergent surfactants include the amine oxide surfactants having the formula:
  • R 3 (OR 4 ) x N(O) (R 5 ) 2
  • R 3 is an alkyl, hydroxyalkyl, or alkyl phenyl group or mixtures thereof containing from about 8 to about 22 carbon atoms
  • R 4 is an alkylene or hydroxyalkylene group containing from about 2 to about 3 carbon atoms or mixtures thereof
  • x is from 0 to about 3
  • each R 5 is an alkyl or hydroxyalkyl group containing from about 1 to about 3 carbon atoms or a polyethylene oxide group containing from about 1 to about 3 ethylene oxide groups.
  • the R 5 groups can be attached to each other, e.g., through an oxygen or nitrogen atom, to form a ring structure.
  • amine oxide surfactants in particular include C 10 -C 18 alkyl dimethyl amine oxides and C 8 -C 12 alkoxy ethyl dihydroxy ethyl amine oxides.
  • Cationic surfactants can also be included in the compositions of the present invention.
  • Cationic surfactants include the ammonium surfactants such as alkyldimethyl ammonium halogenides, and those surfactants having the formula: [R 2 (OR 3 ) y ] [R 4 (OR 3 ) y ] 2 R 5 N ⁇ X ⁇
  • R 2 is an alkyl or alkyl benzyl group having from about 8 to about 18 carbon atoms in the alkyl chain
  • each R 3 is selected from the group consisting of -CH 2 CH 2 -, -CH 2 CH(CH 3 )-, -CH 2 CH(CH 2 OH)-, -CH 2 CH 2 CH 2 -, and mixtures thereof
  • each R 4 is selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, benzyl, ring structures formed by joining the two R 4 groups, -CH 2 CHOHCHOHCOR 6
  • the total surfactant concentration (alkyl polyglycoside + nonionic sugar cosurfactant(s) + additional surfactants) is generally in the range of from about 0.1% to about 80% of the total composition weight, preferably from about 5% to about 40% by weight and most preferably from about 10% to about 25% by weight.
  • compositions of this invention can utilize other compatible ingredients, including other surfactants, in addition to the mixture of surfactants disclosed hereinabove.
  • the compositions can contain any of the well known ingredients including minor amounts of other surfactants, detergency builders, soil suspending agents, brighteners, abrasives, dyes, fabric conditioning agents, hair conditioning agents, hydrotropes, solvents, fillers, clays, fragrances (e.g. perfumes), electrolytes, enzymes, enzyme stabilizers, phase regulants, suds promoting agents, etc.
  • Suitable ingredients are disclosed in U.S. Patent Nos.
  • the shampoo compositions of this invention can contain any of the additional ingredients known in the art to be suitable for use in shampoos. Listings of suitable additional ingredients, including low levels of other surfactants can be found in U.S. Patent Nos. 4,089,945; 3,987,161; and 3,962,418, each of which are incorporated herein by reference.
  • compositions of this invention may provide foams which may make them valuable for use not only in soap bars, bubble baths, shaving creams, laundry, dishwashing, and washing hair, where a good volume of stable suds and quick rinsability are desirable, but also in a large number of fields of detergency.
  • compositions of this invention may also be particularly valuable for use in the "foam” or "mist” well drilling processes in which the foam is used to carry water and/or soil particles to the surface of the bore hole.
  • a description of such a drilling method can be found in U.S. Pat. Nos. 3,303,896; 3,111,178; 3,130,798; and 3,215,200; incorporated herein by reference.
  • compositions of this invention may be of considerable value in fire fighting or fire prevention processes where a stable foam is used to extinguish a flame or sparks by cutting off the oxygen supply.
  • compositions of this invention may also be valuable in the field of preparing gypsum board, plastic, and resin foams.
  • the foams of this invention may provide a stable relatively thick structure permitting solidification of the resins, plastics, cellulosic particles, etc., into stable foam structures having light densities, thick cell walls and good structural integrity. Examples of forming processes which utilize foaming agents are described in U.S. Pat. Nos. 3,669,898; 4,907,982; and 4,423,720, incorporated herein by reference.
  • composition of this invention may involve making use of their expected exceptional stability to provide temporary insulation for plants when freezing conditions are expected. Such a process is disclosed in U.S. Pat. No.
  • compositions of the invention which are described more fully hereinbelow in the examples, will unexpectedly result in surfactant systems that exhibit better foaming characteristics, better solubility in cleaning compositions and better detergency in cleaning compositions.
  • compositions of this invention include all of the above and many more.
  • compositions of the invention can be prepared.
  • a typical shampoo composition according to the present invention comprises (percentages by weight):
  • a typical shaving cream composition according to the present invention comprises (percentages by weight):
  • a typical soap bar composition according to the present invention comprises (percentages by weight):
  • a typical liquid detergent composition according to the present invention comprises (percentages by weight):
  • a typical light duty liquid detergent composition according to the present invention comprises (percentages by weight):
  • a typical powdered detergent composition according to the present invention comprises (percentages by weight):

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Abstract

The invention relates to alkyl polyglycoside surfactant compositions which comprise one or more nonionic sugar cosurfactants.

Description

COMPOSITIONS BASED ON APG AND AT LEAST ONE ADDITIONAL NONIONIC SUGAR COSURFACTANT.
Field of the Invention
The invention relates to alkyl polyglycoside compositions which comprise one or more nonionic sugar cosurfactants.
Summary of the Invention
The present invention relates to compositions comprising:
(a) an alkyl polyglycoside surfactant having the formula R1O(R2O)b(Z)a I
wherein R1 is a monovalent organic radical having from about 6 to about 30 carbon atoms; R1 is divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; and a is a number having a value from 1 to about 6;
(b) one or more nonionic sugar cosurfactants; with the proviso that when the nonionic sugar cosurfactant is a polyhydroxy fatty acid amide or an aldobionamide the composition must contain two or more of said sugar cosurfactants; further provided that when the nonionic sugar cosurfactant is a mixture of a polyhydroxy fatty acid amide and an aldobionamide the composition must contain at least one additional sugar cosurfactant; and
(c) optionally one or more additional surfactants selected from the group consisting of anionic, zwitterionic, amphoteric, nonionic and cationic surfactants; wherein the weight ratio of (a)+(b):(c) is equal to from about 1:10 to about 10:1; and wherein the weight ratio of (b):(a) is equal to from about 1:3 to 3:1.
It is expected that the compositions of the invention will be useful in laundry, personal cleaning products, dishwashing, fire fighting, oil well drilling, ore benefication, solution mining, washing hair, and preparation of foamed solid structures applications.
In preferred compositions of the invention the nonionic sugar cosurfactant is selected from the group consisting of alkyl glucose esters, aldobionamides, gluconamides, glyceramides, glyceroglycolipids and polyhydroxy fatty acid amides.
Detailed Description Inclusive of the Preferred
Embodiments
Alkyl Polvσlvcoside Surfactants
The alkyl polyglycosides which can be used in the compositions according to the invention have the formula I
R1O(R2O)b(Z)a I
wherein R1 is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6. Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero. Such alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, or PLANTAREN® surfactants from Henkel Corporation, Ambler, PA., 19002. Examples of such surfactants include but are not limited to:
1. APG® 225 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
2. APG® 425 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.6.
3. APG® 625 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
4. APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
5. GLUCOPON® 600 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
6. PLANTAREN® 2000 Surfactant - a C8.16 alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
7. PLANTAREN® 1300 Surfactant - a C12-16 alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
Other examples include alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I wherein Z represents a moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is a number having a value from 1 to about 6; b is zero; and R1 is an alkyl radical having from 8 to 20 carbon atoms. The compositions are characterized in that they have increased surfactant properties and an HLB in the range of about 10 to about 16 and a non-Flory distribution of glycosides, which is comprised of a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3. Such compositions, also known as peaked alkyl polyglycosides, can be prepared by separation of the monoglycoside from the original reaction mixture of alkyl monoglycoside and alkyl polyglycosides after removal of the alcohol. This separation may be carried out by molecular distillation and normally results in the removal of about 70-95% by weight of the alkyl monoglycosides. After removal of the alkyl monoglycosides, the relative distribution of the various components, mono- and poly-glycosides, in the resulting product changes and the concentration in the product of the polyglycosides relative to the monoglycoside increases as well as the concentration of individual polyglycosides to the total, i.e. DP2 and DP3 fractions in relation to the sum of all DP fractions. Such compositions are disclosed in U.S. patent 5,266,690, the entire contents of which are incorporated herein by reference.
NONIONIC SUGAR SURFACTANTS
The term nonionic sugar cosurfactant as used herein refers to surfactants that are based on saccharide moieties. Representative examples of such nonionic sugar cosurfactants include, but are not limited thereto, alkyl glucose ester, aldobionamide, gluconamide, glyceramide, glyceroglycolipid and polyhydroxy fatty acid amide surfactants which are described more fully hereinbelow.
The alkyl glucose ester sugar cosurfactants are generally disclosed in U.S. patent Nos. 5,109,127 and 5,190,747 the entire contents of both of which are incorporated herein by reference. These sugar cosurfactants have the general formula:
Figure imgf000007_0001
wherein R represents a fatty acid residue of 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms and R1 represents an alkyl group having 2 to 6 carbon atoms. Representative examples of such alkyl glucose esters are 1-ethyl-6-caprylglucoside, 1-ethyl-6-laurylglucoside, 1-butyl-6- caprylglucoside, 1-ethyl-6-palmitylglucoside and 1-ethyl-6-oleylglucoside.
The aldobionamide sugar cosurfactants are generally disclosed in U.S. Patent No. 5,310,542 and in published European Patent Application No. 550,281 both of which are incorporated herein by reference. An Aldobionamide is generally defined as the amide of an aldobionic acid or aldobionolactone and an aldobionic acid in turn is defined as a sugar substance (e.g. any cyclic sugar) in which the aldehyde group has been replaced by a carboxylic acid which upon drying is capable of cyclizing to form an aldonolactone. The aldobionamides can be based on compounds comprising two saccharide units, e.g. lactobionamides, maltobionamides, cellobionamides, melibionamides, or gentiobionamides, or they can be based on compounds comprising more than two saccharide units provided that the polysaccharide has a terminal sugar unit with an aldehyde group available.
The preferred aldobionamides of the present invention are lactobionamides of the formula
Figure imgf000008_0001
wherein R1 and R2 are the same or different and are selected from hydrogen and an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g. alkyl groups and alkenyl groups which groups may also include a heteroatom such as N, O, S, present, for instance, as an amide, carboxy, ether and/or saccharide moiety) except that R1 and R2 cannot simultaneously be hydrogen. The aliphatic hydrocarbon radical preferably contains up to 24 carbon atoms, most preferably from 8 to 18 carbon atoms. Representative examples of such lactobionamides are N-propyl lactobionamide, N-pentyl lactobionamide, N-decyl lactobionamide, N-hexadecyl lactobionamide, N-oleyl lactobionamide, N-dodecyl-N-methyl lactobionamide, and N-dodecyloxypropyl lactobionamide.
The gluconamide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,386 the entire contents of which is incorporated herein by reference. These cosurfactants have the general formula:
HOCH2-(CHOH)m-C(O)-NHR wherein m is an integer from 2 to 5; and R is a straight or branched, saturated or unsaturated aliphatic hydrocarbon having 4 to about 24 carbon atoms, preferably 8 to 24 carbon atoms, which R group can also contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur. Representative examples of such cosurfactants areN-octylerythronamide, N-decylerythronamide, N- dodecylerythronamide, N-tetradecylerythronamide, N- decylxylonamide and N-dodecylxylonamide.
The glyceramide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,387 the entire contents of which is incorporated herein by reference. These cosurfactants have the general formula:
HOCH2CH(OH)C(O)NHR wherein R is a C8 to C24 straight or branched chained, saturated or unsaturated aliphatic hydrocarbon in which the R group may also be substituted by a heteroatom selected from oxygen, nitrogen and sulfur. Representative examples of such cosurfactants are N-octylglyceramide, N-decylglyceramide and N-hexadecylglyceramide.
The glyceroglycolipid sugar cosurfactants are generally disclosed in U.S. Patent 5,358,656, and published European Patent Application No. 550,279 the disclosure of each of which is incorporated herein by reference. The glyceroglycolipids can be of the formula:
A1-O-CH2-CH (B)-CH2NRR1 wherein A1 is a saccharide, preferably having one or more saccharide units, more preferably a mono or disaccharide and most preferably a monosaccharide such as glucose or galactose; R and R1 are the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having from 1 to about 24, preferably from about 6 to about 18 carbon atoms; B is OH or a NR2R3 group, wherein R2 and R3 may be the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having 1 to 24, preferably from 6 to 18 carbon atoms, and NRR1 and B are positionally interchangeable. Representative examples of such cosurfactants are 3-(butylamino)-2-hydroxypropyl-β-D-galactopyranoside, 3-(octylamino)-2-hydroxypropyl-β-D-galactopyranoside, 3-(eicosylamino)-2-hydroxypropyl-β-D- galactopyranoside, 3- (butylamino)-2-hydroxypropyl-β-D-glucopyranoside, and 3-(pentylamino)-2-hydroxypropyl-β-D-mannopyranoside.
Other glyceroglycolipid cosurfactants are disclosed in published European Patent Application No. 550,280 which is incorporated herein by reference. These cosurfactants are of the formula:
A1-O-CH2-CH(OR1)-CH2OR wherein A1 is from 1 to 4 saccharide units and more preferably represents a mono or disaccharide, and most preferably a monosaccharide, for example, glucose or galactose; R and R1 are the same or different and are hydrogen, or a branched or unbranched, saturated or unsaturated, hydrocarbon radical having from 1 to 24 carbon atoms, preferably from 6 to 18 carbon atoms. Representative examples of such cosurfactants are 3-(butyloxy)-2-hydroxypropyl-β-D-galactopyranoside, 3-(eicosyloxy)-2-hydroxypropyl-β-D-galactopyranoside, 3-(decyloxy)-2-hydroxypropyl-β-D-galactopyranoside, 3-(butyloxy)-2-hydroxypropyl-β-D-glucopyranoside, 3-(octyloxy)-2-hydroxypropyl-β-D-mannopyranoside, 3-(tetradecyloxy)-2-hydroxypropyl-β-D-lactoside, 3-(octadecyloxy)-2-hydroxypropyl-β-D-maltoside, 3-(octyloxy)-2-hydroxypropyl-β-D-galactotrioside, and 3-(dodecyloxy)-2-hydroxypropyl-β-D-cellotrioside.
The polyhydroxy fatty acid amide sugar cosurfactants are generally disclosed in U.S. Patent Nos. 5,174,927, 5,223,179 and 5,332,528 the entire disclosure of each of which is incorporated herein by reference. The polyhydroxy fatty acid amide surfactant component of the present invention comprises compounds of the structural formula: R2C(O)N(R1)Z wherein : R1 is H, C1-C4 hydrocarbyl , 2-hydroxy ethyl , 2-hydroxy propyl or a mixture thereof, preferably C1-C4 alkyl, more preferably C1 or C2 alkyl, most preferably C1 alkyl (i.e., methyl); and R2 is a C5-C31 hydrocarbyl, preferably straight chain C7-C19 alkyl or alkenyl, more preferably straight chain C6-C17 alkyl or alkenyl, most preferably straight chain C11-C17 alkyl or alkenyl, or mixture thereof; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof. Z preferably will be derived from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl. Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose. As raw materials, high dextrose corn syrup, high fructose corn syrup, and high maltose corn syrup can be utilized as well as the individual sugars listed above. These corn syrups may yield a mix of sugar components for Z. It should be understood that it is by no means intended to exclude other suitable raw materials. Z preferably will be selected from the group consisting of -CH2-(CHOH)n-CH2OH, -CH(CH2OH) -(CHOH)n-1-CH2OH, -CH2-(CHOH)2(CHOR') (CHOH)-CH2OH, where n is an integer from 3 to 5, inclusive, and R' is H or a cyclic or aliphatic monosaccharide, and alkoxylated derivatives thereof. Most preferred are glycityls wherein n is 4, particularly -CH2-(CHOH)4-CH2OH.
In the above Formula R1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
R2C(O)N< can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
Z can be 1-deoxyglucityl, 2-deoxyfructityl, 1-deoxymaltityl, 1-deoxylactityl, 1-deoxygalactityl, 1-deoxymannityl, 1-deoxymaltotriotityl, etc.
Representative examples of such cosurfactants are N-methyl-N-1-deoxyglucityl cocoamide and N-methyl-N-1- deoxyglucityl tallowamide.
Other suitable polyhydroxy fatty acid amide cosurfactants (see U.S. Patent Nos. 5,223,179 and
5,338,491, the entire contents of each which are incorporated herein by reference) are those of the formula:
RC(O)N(R1)CH2CH(OH)CH2OH wherein R is a C7-C21 hydrocarbyl species, i.e. coconut, tallow, palm fatty alkyl and oleyl, and R1 is a C1 to C6 hydrocarbyl or substituted hydrocarbyl species, i.e. N-alkyl-N-(1,2-propanediol) and N-hydroxyalkyl-N-1,2-propane diol fatty acid amides. Representative examples of such cosurfactants are the tallow amide of 3-[2- (hydroxyethyl)amino]-1,2-propanediol (HEAPD), the palmitate amide of 3-methylamino-1,2-propanediol (MAPD) and the lauramide of MAPD.
ADDITIONAL SURFACTANTS
(a) anionic surfactants
Anionic surfactants (suitable ones are generally disclosed in U.S. Patent 4,599,188 the entire contents of which is incorporated herein by reference) can be selected from the group consisting of sulfates, sulfonates, carboxylates and mixtures thereof. The surfactants are neutralized with a cationic moiety or moieties selected from the group consisting of alkali metal, e.g. sodium or potassium, alkaline earth metal, e.g. calcium or magnesium, ammonium, substituted ammonium, including mono-, di-, or tri-. ethanolammonium cations. Mixtures of cations can be desirable. The anionic surfactants which may be useful in the present invention all have detergent properties and are all water soluble or dispersible in water.
One class of surfactants which may be used in this invention is an alkylbenzene sulfonate. The alkyl group can be either saturated or unsaturated, branched or straight chain and is optionally substituted with a hydroxy group. Middle phenyl positions are generally preferred for volume of foaming in light soil conditions. However, in heavier soil conditions phenyl attachment at the 1- or 2-position is preferred.
The preferred alkylbenzene sulfonates contain a straight alkyl chain containing from about 9 to about 25 carbon atoms, preferably from about 10 to about 13 carbon atoms, and the cation is sodium, potassium, ammonium, mono-, di-, or triethanolammonium, calcium or magnesium and mixtures thereof. Magnesium is the preferred cationic moiety. These same cations are preferred for other anionic surfactants and ingredients. The magnesium alkylbenzene sulfonates where the phenyl group is attached near the middle of the alkyl chain are surprisingly better than the ones with the phenyl near the end of the chain when the polysaccharide chain averages greater than about 3 saccharide units. Suitable alkylbenzene sulfonates include C11 alkylbenzene sulfonates with low 2-phenyl content.
Other surfactants which may be used in this invention are carboxylates, e.g. fatty acid soaps and similar surfactants. The soaps can be saturated or unsaturated and can contain various substituents such as hydroxy groups and alpha-sulfonate groups. Preferably, the hydrophobic portion of the soap is a straight chain saturated or unsaturated hydrocarbon. The hydrophobic portion of the soap usually contains from about 6 to about 30 carbon atoms, preferably from about 10 to about 18 carbon atoms.
The cationic moiety (M) for carboxylate surfactants is selected from the group consisting of alkali metal, for example, sodium or potassium, alkaline earth metal, for example, calcium or magnesium, ammonium, or substituted ammonium, including mono-, di-, or triethanolammonium cations. Mixtures of cations can be desirable.
Yet other surfactants are the alkyl (paraffin or olefin) sulfonates, preferably with a more central hydrophilic group, containing from about 6 to about 30 carbon atoms. Examples include C14-15 paraffin sulfonates and C14-16 olefin sulfonates.
In addition to the sulfonate and soap surfactants discussed hereinabove, many other surfactants which contain sulfonate or carboxylate groups can be used in the compositions of the invention. These other surfactants may include, for example, the sulfosuccinate surfactants disclosed in U.S. Patent 5,015,414 the entire contents of which is incorporated herein by reference, and the dialkyl sulfosuccinate surfactants disclosed in U.S. Patent 4,839,098, the entire contents of which is incorporated herein by reference.
(b) zwitterionic surfactants
One group of surfactants that are of interest because of their superior detergency are the zwitterionic surfactants which contain both a cationic group, either ammonium, phosphonium, sulfonium or mixtures thereof and a sulfonate or carboxylate group. Preferably there are at least about four atoms separating the cationic and anionic groups. Suitable zwitterionic surfactants are disclosed in U.S. Pat. Nos. 4,159,277; 3,928,251; 3,925,262; 3,929,678; 3,227,749; 3,539,521; 3,383,321; 3,390,094; and 3,239,560, incorporated herein by reference. Such surfactants are especially desirable for shampoos.
(c) amphoteric surfactants
Another group of surfactants are the amphoteric surfactants which have the same general structure as the zwitterionic surfactants but with an amine group instead of the quaternary ammonium group. Suitable amphoteric surfactants are disclosed, for example, in U.S. Patent 3,929,678, which is incorporated herein by reference.
(d) nonionic surfactants
Suitable nonionic detergent surfactants are generally disclosed in U.S. Pat. No. 3,929,678, Laughlin et al., issued Dec. 30, 1975, at column 13, line 14 through column 16, line 6, incorporated herein by reference. Exemplary, non-limiting classes of useful nonionic surfactants are listed below.
The polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols. In general, the polyethylene oxide condensates are preferred. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 12 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide. In a preferred embodiment, the ethylene oxide is present in an amount equal to from about 5 to about 25 moles of ethylene oxide per mole of alkyl phenol. Commercially available nonionic surfactants of this type include IGEPAL® CO-630, marketed by the GAF Corporation; and TRITON® X-45, X-114, X-100, and X-102, all marketed by the Rohm & Haas Company. This category includes, for example, alkyl phenol alkoxylates such as the alkylphenol ethoxylates.
The condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide. The alkyl chain of the aliphatic alcohol can either be straight or branched, primary or secondary, and generally contains from about 8 to about 22 carbon atoms. Particularly preferred are the condensation products of alcohols having an alkyl group containing from about 10 to about 20 carbon atoms with from about 2 to about 18 moles of ethylene oxide per mole of alcohol. Examples of commercially available nonionic surfactants of this type include TERGITOL® 15-S-9
(the condensation product of C11-C15 linear secondary alcohol with 9 moles ethylene oxide), TERGITOL® 24-L-6 NMW (the condensation product of C12-C14 primary alcohol with 6 moles ethylene oxide with a narrow molecular weight distribution), both marketed by Union Carbide Corporation; NEODOL® 45-9 (the condensation product of C14-C15 linear alcohol with 9 moles of ethylene oxide), NEODOL® 23-6.5
(the condensation product of C12-C13 linear alcohol with 6.5 moles of ethylene oxide), NEODOL® 45-7 (the condensation product of C14-C15 linear alcohol with 7 moles of ethylene oxide), NEODOL® 45-4 (the condensation product of C14-C15 linear alcohol with 4 moles of ethylene oxide), marketed by Shell Chemical Company, and KYRO® EOB (the condensation product of C13-C15 alcohol with 9 moles ethylene oxide), marketed by The Procter & Gamble Company. These surfactants are commonly referred to as alkyl ethoxylates.
The condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol. The hydrophobic portion of these compounds preferably has a molecular weight of from about 1500 to about 1800 and exhibits water insolubility. The addition of polyoxyethylene moieties to this hydrophobic portion tends to increase the water solubility of the molecule as a whole, and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50% of the total weight of the condensation product, which corresponds to condensation with up to about 40 moles of ethylene oxide. Examples of compounds of this type include certain of the commercially-available PLURONIC® surfactants, marketed by BASF.
The condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine. The hydrophobic moiety of these products consists of the reaction product of ethylenediamine and excess propylene oxide, and generally has a molecular weight of from about 2500 to about 3000. This hydrophobic moiety is condensed with ethylene oxide to the extent that the condensation product contains from about 40% to about 80% by weight of polyoxyethylene and has a molecular weight of from about 5,000 to about 11,000. Examples of this type of nonionic surfactant include certain of the commercially available TETRONIC® compounds, marketed by BASF.
Semi-polar nonionic surfactants are a special category of nonionic surfactants which include water-soluble amine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms.
Semi-polar nonionic detergent surfactants include the amine oxide surfactants having the formula:
R3(OR4)xN(O) (R5)2 wherein R3 is an alkyl, hydroxyalkyl, or alkyl phenyl group or mixtures thereof containing from about 8 to about 22 carbon atoms; R4 is an alkylene or hydroxyalkylene group containing from about 2 to about 3 carbon atoms or mixtures thereof; x is from 0 to about 3; and each R5 is an alkyl or hydroxyalkyl group containing from about 1 to about 3 carbon atoms or a polyethylene oxide group containing from about 1 to about 3 ethylene oxide groups. The R5 groups can be attached to each other, e.g., through an oxygen or nitrogen atom, to form a ring structure.
These amine oxide surfactants in particular include C10-C18 alkyl dimethyl amine oxides and C8-C12 alkoxy ethyl dihydroxy ethyl amine oxides.
(e) cationic surfactants
Cationic surfactants can also be included in the compositions of the present invention. Cationic surfactants include the ammonium surfactants such as alkyldimethyl ammonium halogenides, and those surfactants having the formula: [R2(OR3)y] [R4(OR3)y]2R5N⊕ X⊖ wherein R2 is an alkyl or alkyl benzyl group having from about 8 to about 18 carbon atoms in the alkyl chain, each R3 is selected from the group consisting of -CH2CH2-, -CH2CH(CH3)-, -CH2CH(CH2OH)-, -CH2CH2CH2-, and mixtures thereof; each R4 is selected from the group consisting of C1-C4 alkyl, C1-C4 hydroxyalkyl, benzyl, ring structures formed by joining the two R4 groups, -CH2CHOHCHOHCOR6 -CHOHCH2OH wherein R6 is any hexose or hexose polymer having a molecular weight less than about 1000, and hydrogen when y is not 0; R5 is the same as R4 or is an alkyl chain wherein the total number of carbon atoms of R2 plus R5 is not more than about 18; each y is from 0 to about 10 and the sum of the y values is from 0 to about 15; and X is any compatible anion. Cationic surfactants of this type are generally described in U.S. Patent 5,332,528, the entire contents of which is incorporated herein by reference.
Other cationic surfactants useful herein are also described in U.S. Pat. No. 4,228,044, issued Ocober 14, 1980, incorporated herein by reference.
In the compositions of the invention the total surfactant concentration (alkyl polyglycoside + nonionic sugar cosurfactant(s) + additional surfactants) is generally in the range of from about 0.1% to about 80% of the total composition weight, preferably from about 5% to about 40% by weight and most preferably from about 10% to about 25% by weight.
ADDITIONAL INGREDIENTS
The compositions of this invention can utilize other compatible ingredients, including other surfactants, in addition to the mixture of surfactants disclosed hereinabove. In detergent compositions the compositions can contain any of the well known ingredients including minor amounts of other surfactants, detergency builders, soil suspending agents, brighteners, abrasives, dyes, fabric conditioning agents, hair conditioning agents, hydrotropes, solvents, fillers, clays, fragrances (e.g. perfumes), electrolytes, enzymes, enzyme stabilizers, phase regulants, suds promoting agents, etc. Suitable ingredients are disclosed in U.S. Patent Nos. 4,166,039; 4,157,978; 4,056,481; 4,049,586; 4,035,257; 4,019,998; 4,000,080; and 3,983,078, and in European Patent Application No. 550,280, published July 7, 1993; European Patent Application No. 550,281, published July 7, 1993; and European Patent Application No. 550,279, published July 7, 1993; the entire contents of each of which are incorporated herein by reference. The shampoo compositions of this invention can contain any of the additional ingredients known in the art to be suitable for use in shampoos. Listings of suitable additional ingredients, including low levels of other surfactants can be found in U.S. Patent Nos. 4,089,945; 3,987,161; and 3,962,418, each of which are incorporated herein by reference.
Methods
It is contemplated that the compositions of this invention may provide foams which may make them valuable for use not only in soap bars, bubble baths, shaving creams, laundry, dishwashing, and washing hair, where a good volume of stable suds and quick rinsability are desirable, but also in a large number of fields of detergency.
It is contemplated that the compositions of this invention may also be particularly valuable for use in the "foam" or "mist" well drilling processes in which the foam is used to carry water and/or soil particles to the surface of the bore hole. A description of such a drilling method can be found in U.S. Pat. Nos. 3,303,896; 3,111,178; 3,130,798; and 3,215,200; incorporated herein by reference.
It is also contemplated that the compositions of this invention may be of considerable value in fire fighting or fire prevention processes where a stable foam is used to extinguish a flame or sparks by cutting off the oxygen supply. This includes fire fighting and foaming runaways for crash-landings as disclosed in U.S. Pat. Nos. 2,514,310; 3,186,943; 3,422,011; 3,457,172; 3,479,285; and 3,541,010, incorporated herein by reference.
It is contemplated that the compositions of this invention may also be valuable in the field of preparing gypsum board, plastic, and resin foams. The foams of this invention may provide a stable relatively thick structure permitting solidification of the resins, plastics, cellulosic particles, etc., into stable foam structures having light densities, thick cell walls and good structural integrity. Examples of forming processes which utilize foaming agents are described in U.S. Pat. Nos. 3,669,898; 4,907,982; and 4,423,720, incorporated herein by reference.
It is also contemplated that the flotation of minerals so as to concentrate the mineral values, e.g., in the foam (beneficiation), can be carried out advantageously using the compositions of this invention. Such processes are described in U.S. Pat. Nos. 4,147,644; 4,139,482; 4,139,481; 4,138,350; 4,090,972; and 3,640,862, incorporated herein by reference.
It is further contemplated that a special advantage of the composition of this invention may involve making use of their expected exceptional stability to provide temporary insulation for plants when freezing conditions are expected. Such a process is disclosed in U.S. Pat. No.
3,669,898, incorporated herein by reference.
It is further contemplated that the compositions of the invention, which are described more fully hereinbelow in the examples, will unexpectedly result in surfactant systems that exhibit better foaming characteristics, better solubility in cleaning compositions and better detergency in cleaning compositions.
The range of utilities which are possible with the compositions of this invention include all of the above and many more.
The following examples will further illustrate the compositions of the present invention without, however, limiting it thereto.
WORKING EXAMPLES
Following standard procedures which are well known to the skilled formulator, it is contemplated that the following compositions of the invention can be prepared.
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
A typical shampoo composition according to the present invention comprises (percentages by weight):
Figure imgf000027_0001
A typical shaving cream composition according to the present invention comprises (percentages by weight):
Figure imgf000027_0002
A typical soap bar composition according to the present invention comprises (percentages by weight):
Figure imgf000027_0003
A typical liquid detergent composition according to the present invention comprises (percentages by weight):
Figure imgf000028_0001
A typical light duty liquid detergent composition according to the present invention comprises (percentages by weight):
Figure imgf000028_0002
A typical powdered detergent composition according to the present invention comprises (percentages by weight):
Figure imgf000028_0003

Claims

What is claimed is:
1. A composition comprising:
(a) an alkyl polyglycoside surfactant having the formula
R1O(R2O)b(Z)a I
wherein R1 is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; and a is a number having a value from 1 to about 6;
(b) one or more nonionic sugar cosurfactants; with the proviso that when the nonionic sugar cosurfactant is a polyhydroxy fatty acid amide or an aldobionamide the composition must contain two or more of said sugar cosurfactants; further provided that when the nonionic sugar cosurfactant is a mixture of a polyhydroxy fatty acid amide and an aldobionamide the composition must contain at least one additional sugar cosurfactant; and
(c) optionally one or more additional surfactants selected from the group consisting of anionic, zwitterionic, amphoteric, nonionic and cationic surfactants; wherein the weight ratio of (a)+(b):(c) is equal to from about 1:10 to about 10:1; and wherein the weight ratio of (b): (a) is equal to from about 1:3 to 3:1.
2. A composition according to claim 1 wherein said nonionic sugar cosurfactants are selected from the group consisting of alkyl glucose esters, aldobionamides, gluconamides, glyceramides, glyceroglycolipids and polyhydroxy fatty acid amides.
3. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant and an alkyl glucose ester cosurfactant.
4. A composition according to claim 3 which further comprises an aldobionamide cosurfactant.
5. A composition according to claim 3 which further comprises a gluconamide cosurfactant.
6. A composition according to claim 3 which further comprises a glyceramide cosurfactant.
7. A composition according to claim 3 which further comprises a glyceroglycolipid cosurfactant.
8. A composition according to claim 3 which further comprises a polyhydroxy fatty acid amide cosurfactant.
9. A composition according to claim 4 which further comprises a gluconamide cosurfactant.
10. A composition according to claim 4 which further comprises a glyceramide cosurfactant.
11. A composition according to claim 4 which further comprises a glyceroglycolipid cosurfactant.
12. A composition according to claim 4 which further comprises a polyhydroxy fatty acid amide cosurfactant.
13. A composition according to claim 9 which further comprises a glyceramide cosurfactant.
14. A composition according to claim 9 which further comprises a glyceroglycolipid cosurfactant.
15. A composition according to claim 9 which further comprises a polyhydroxy fatty acid amide cosurfactant.
16. A composition according to claim 13 which further comprises a glyceroglycolipid cosurfactant.
17. A composition according to claim 13 which further comprises a polyhydroxy fatty acid amide cosurfactant.
18. A composition according to claim 16 which further comprises a polyhydroxy fatty acid amide cosurfactant.
19. A composition according to claim 5 which further comprises a glyceramide cosurfactant.
20. A composition according to claim 5 which further comprises a glyceroglycolipid cosurfactant.
21. A composition according to claim 5 which further comprises a polyhydroxy fatty acid amide cosurfactant.
22. A composition according to claim 6 which further comprises a glyceroglycolipid cosurfactant.
23. A composition according to claim 6 which further comprises a polyhydroxy fatty acid amide cosurfactant.
24. A composition according to claim 7 which further comprises a polyhydroxy fatty acid amide cosurfactant.
25. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant, an aldobionamide cosurfactant and a gluconamide cosurfactant.
26. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant, an aldobionamide cosurfactant and a glyceramide cosurfactant.
27. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant, an aldobionamide cosurfactant and a glyceroglycolipid cosurfactant.
28. A composition according to claim 25 which further comprises a glyceramide cosurfactant.
29. A composition according to claim 25 which further comprises a glyceroglycolipid cosurfactant.
30. A composition according to claim 25 which further comprises a polyhydroxy fatty acid amide cosurfactant.
31. A composition according to claim 26 which further comprises a glyceroglycolipid cosurfactant.
32. A composition according to claim 26 which further comprises a polyhydroxy fatty acid amide cosurfactant.
33. A composition according to claim 27 which further comprises a polyhydroxy fatty acid amide cosurfactant.
34. A composition according to claim 31 which further comprises a gluconamide cosurfactant.
35. A composition according to claim 32 which further comprises a gluconamide cosurfactant.
36. A composition according to claim 34 which further comprises a polyhydroxy fatty acid amide cosurfactant.
37. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant and a gluconamide cosurfactant.
38. A composition according to claim 37 which further comprises a glyceramide cosurfactant.
39. A composition according to claim 37 which further comprises a glyceroglycolipid cosurfactant.
40. A composition according to claim 37 which further comprises a polyhydroxy fatty acid amide cosurfactant.
41. A composition according to claim 38 which further comprises a glyceroglycolipid cosurfactant.
42. A composition according to claim 38 which further comprises a polyhydroxy fatty acid amide cosurfactant.
43. A composition according to claim 39 which further comprises a polyhydroxy fatty acid amide cosurfactant.
44. A composition according to claim 43 which further comprises a glyceramide cosurfactant.
45. A composition according to claim 44 which further comprises an alkyl glucose ester cosurfactant.
46. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant and a glyceramide cosurfactant.
47. A composition according to claim 46 which further comprises a glyceroglycolipid cosurfactant.
48. A composition according to claim 46 which further comprises a polyhydroxy fatty acid amide cosurfactant.
49. A composition according to claim 47 which further comprises a polyhydroxy fatty acid amide cosurfactant.
50. A composition according to claim 49 which further comprises an alkyl glucose ester cosurfactant.
51. A composition according to claim 49 which further comprises an aldobionamide cosurfactant.
52. A composition according to claim 2 which comprises an alkyl polyglycoside surfactant and a glyceroglycolipid cosurfactant.
53. A composition according to claim 52 which further comprises a polyhydroxy fatty acid amide cosurfactant.
54. A composition according to claim 1 which is a shampoo.
55. A composition according to claim 1 which is a shaving cream.
56. A composition according to claim 1 which is a soap bar.
57. A composition according to claim 1 which is a liquid detergent.
58. A composition according to claim 1 which is a light duty liquid detergent.
59. A composition according to claim 1 which is a powdered detergent.
PCT/US1996/003643 1995-03-31 1996-03-29 Compositions based on apg and at least one additional nonionic sugar cosurfactant WO1996029977A1 (en)

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AU53650/96A AU5365096A (en) 1995-03-31 1996-03-29 Compositions based on apg and at least one additional nonion ic sugar cosurfactant
BR9607946A BR9607946A (en) 1995-03-31 1996-03-29 Composition
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0849354A1 (en) * 1996-12-20 1998-06-24 Unilever Plc Softening compositions
US6686323B2 (en) 2001-06-12 2004-02-03 Schlumberger Technology Corporation Surfactant compositions for well cleaning
EP2551327A1 (en) * 2011-07-26 2013-01-30 Halliburton Energy Services, Inc. Thermally stable, nonionic foaming agent for foam fracturing fluids
GB2503346A (en) * 2012-05-25 2013-12-25 Rhodia Operations Method of unloading liquid from a hydrocarbon reservoir using first and second surfactants
WO2016146303A1 (en) * 2015-03-19 2016-09-22 Clariant International Ltd Biodegradable sugar-amide-surfactants for enhanced oil recovery
WO2023014952A1 (en) * 2021-08-05 2023-02-09 Ecolab Usa Inc. Sugar/gluconoamide alkoxylate compositions and uses thereof
US12241011B2 (en) 2021-08-05 2025-03-04 Ecolab Usa Inc. Polyamine-polyesters as corrosion inhibition

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487262A2 (en) * 1990-11-20 1992-05-27 Unilever Plc Detergent compositions
EP0550281A2 (en) * 1991-12-31 1993-07-07 Unilever Plc Compositions comprising nonionic glycolipid surfactants
US5338491A (en) * 1992-03-26 1994-08-16 The Proctor & Gamble Co. Cleaning compositions with glycerol amides
US5352387A (en) * 1992-11-25 1994-10-04 Lever Brothers Company Alkyl glyceramide surfactants and compositions comprising these surfactants
US5352386A (en) * 1992-11-25 1994-10-04 Lever Brothers Company Compositions free of boron comprising N-alkylerythronamides and N-alkylxylonamides as surfactants
US5358656A (en) * 1991-12-31 1994-10-25 Lever Brothers Company, Division Of Conopco, Inc. Compositions comprising glyceroglycolipids having an amine linkage as a surfactant or cosurfactant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487262A2 (en) * 1990-11-20 1992-05-27 Unilever Plc Detergent compositions
EP0550281A2 (en) * 1991-12-31 1993-07-07 Unilever Plc Compositions comprising nonionic glycolipid surfactants
US5358656A (en) * 1991-12-31 1994-10-25 Lever Brothers Company, Division Of Conopco, Inc. Compositions comprising glyceroglycolipids having an amine linkage as a surfactant or cosurfactant
US5338491A (en) * 1992-03-26 1994-08-16 The Proctor & Gamble Co. Cleaning compositions with glycerol amides
US5352387A (en) * 1992-11-25 1994-10-04 Lever Brothers Company Alkyl glyceramide surfactants and compositions comprising these surfactants
US5352386A (en) * 1992-11-25 1994-10-04 Lever Brothers Company Compositions free of boron comprising N-alkylerythronamides and N-alkylxylonamides as surfactants

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0849354A1 (en) * 1996-12-20 1998-06-24 Unilever Plc Softening compositions
WO1998028390A1 (en) * 1996-12-20 1998-07-02 Unilever Plc Softening compositions
US6686323B2 (en) 2001-06-12 2004-02-03 Schlumberger Technology Corporation Surfactant compositions for well cleaning
EP2551327A1 (en) * 2011-07-26 2013-01-30 Halliburton Energy Services, Inc. Thermally stable, nonionic foaming agent for foam fracturing fluids
US8770295B2 (en) 2011-07-26 2014-07-08 Halliburton Energy Services, Inc. Thermally stable, nonionic foaming agent for foam fracturing fluids
GB2503346A (en) * 2012-05-25 2013-12-25 Rhodia Operations Method of unloading liquid from a hydrocarbon reservoir using first and second surfactants
WO2016146303A1 (en) * 2015-03-19 2016-09-22 Clariant International Ltd Biodegradable sugar-amide-surfactants for enhanced oil recovery
CN107429156A (en) * 2015-03-19 2017-12-01 科莱恩国际有限公司 For improving the biodegradable sugared acidamide surfactant of oil recovery
EA034145B1 (en) * 2015-03-19 2020-01-09 Клариант Интернэшнл Лтд Biodegradable sugar-amide-surfactants for enhanced oil recovery
CN107429156B (en) * 2015-03-19 2020-05-01 科莱恩国际有限公司 Biodegradable sugar-amide-surfactants for enhanced oil recovery
WO2023014952A1 (en) * 2021-08-05 2023-02-09 Ecolab Usa Inc. Sugar/gluconoamide alkoxylate compositions and uses thereof
US12241011B2 (en) 2021-08-05 2025-03-04 Ecolab Usa Inc. Polyamine-polyesters as corrosion inhibition

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AU5365096A (en) 1996-10-16
MX9707233A (en) 1997-11-29

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