WO2001019507A1 - Melanges de tensioactifs ternaires comprenant des tensioactifs cationiques, anioniques et des tensioactifs de pontage et procedes de preparation de ces melanges - Google Patents

Melanges de tensioactifs ternaires comprenant des tensioactifs cationiques, anioniques et des tensioactifs de pontage et procedes de preparation de ces melanges Download PDF

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WO2001019507A1
WO2001019507A1 PCT/US2000/023719 US0023719W WO0119507A1 WO 2001019507 A1 WO2001019507 A1 WO 2001019507A1 US 0023719 W US0023719 W US 0023719W WO 0119507 A1 WO0119507 A1 WO 0119507A1
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surfactant
carbon atoms
average
anionic
alkyl
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PCT/US2000/023719
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Daniela T. Bratescu
Randy J. Bernhardt
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Stepan Company
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Priority to AU69453/00A priority Critical patent/AU6945300A/en
Priority to CA002397811A priority patent/CA2397811A1/fr
Priority to EP00957899A priority patent/EP1257350A1/fr
Publication of WO2001019507A1 publication Critical patent/WO2001019507A1/fr

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    • 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
    • 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
    • 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
    • C11D1/65—Mixtures of anionic 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
    • C11D1/86—Mixtures of anionic, cationic, and 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the present invention relates to surfactant blends comprising a mixture of at least one cationic surfactant, at least one anionic surfactant and optionally at least one "bridging surfactant" selected from semi-polar nonionic, ethoxylated alkanolamide, and amphote ⁇ c/zwitte ⁇ onic surfactants, and mixtures thereof More specifically, the invention relates to stable, synergistic mixtures of cationic, anionic, and bridging surfactants that are useful as bulk surfactant blends
  • anionic-cationic surfactant mixtures also have shown antagonistic effects relative to the properties of the individual surfactant components
  • Chobanu et al Izv Akad Nauk Mold SSR, Ser Biol Khim Nauk , 5, p 66 (1982)
  • most anionic-cationic surfactant mixtures studied are insoluble or only slightly soluble in water
  • practical use of anionic- cationic surfactant mixtures has been very limited in areas where a relatively high concentration of surfactants is needed (see U S Pat No 5,472,455, to Mehreteab, issued Dec 5, 1995)
  • there is a need for soluble anionic-cationic surfactant mixtures At present, very few anionic-cationic surfactant mixtures have been found which produce clear solution phases over a wide concentration range at equimolar composition See generally, Khan, A , Marques, E , Spec Surfactants 1997, 37-80, edited by Robb, I D Blackie Typically, anionic-cationic-cationic
  • anionic-cationic synergism is limited by the formation of an insoluble salt, which typically occurs when the combined number of carbon atoms in the chains of both surfactants totals more than about twenty
  • Surfactant blends of the present invention are useful for preparing a variety of finished consumer cleaning products, including for example, liquid dish detergents, laundry detergents, automatic dishwasher detergents, hand soaps, laundry bars, personal cleansing bars, multi-purpose cleaners, multi-functional shampoos, body washes, and textile treatment compositions
  • Surfactant blends of the present invention also may be employed as surfactants in agricultural and pesticide applications Additionally, the surfactant blends may be utilized in antimicrobial detergent formulations (e g , antimicrobial hard surface cleaners, hand soaps, shampoos, and dish detergents), soft-terg delivery systems and pre-spotter compositions
  • Surfactant blends of the present invention may be prepared in various concentrations and exhibit a wide range of rheological behavior The surfactant blends display excellent detergent and conditioning properties
  • One aspect of the present invention relates to surfactant complexes comprising at least one cationic surfactant, at least one anionic surfactant, and at least one "bridging surfactant" selected from nonionic, semi-polar nonionic, and amphote ⁇ c/zwitterionic surfactants, and mixtures thereof
  • bridging surfactant selected from nonionic, semi-polar nonionic, and amphote ⁇ c/zwitterionic surfactants, and mixtures thereof
  • the present invention furnishes substantially water-soluble ternary surfactant blends which provide improved performance, such as for example, increased surface tension reduction, improved wetting times, and increased foam volume and stability, to detergent and personal care surfactant formulations Additionally, ternary blends of the present invention provide for improved greasy, oily soil removal from surfaces and textiles The blends are also capable of providing conditioning properties to skin, hair and textiles
  • blends of the present invention generally are flowable at concentrations as high as about 80 percent by weight Additionally, the surfactant blends when diluted to a concentration of about 0 1 percent by weight in water generally form a clear aqueous solution substantially free of precipitates
  • flowable means fluid under gravity at ambient conditions (about 1 atmosphere of pressure at about 25°C) without application of mechanical energy
  • clear means allowing at least 50% transmittance measured spectrophotomet ⁇ cally at 700 nanometers using water as the standard for 100% transmittance
  • R-i, R 2 , and R 3 are independently ethyl or methyl, R 4 is an alkyl group having an average of from about 8 to about 16 carbon atoms, and
  • X is halogen, sulfate, methosulfate, ethosulfate, tosylate, acetate, phosphate, nitrate, sulfonate, or carboxylate,
  • an anionic surfactant which is (1) an alkyl sulfate having an average of from about 8 to about 16 carbon atoms,
  • vn a sarcosinate having an average of from about 10 to about 16 carbon atoms, or (vni) a sulfoacetate having an average of from about 12 to about 20 carbon atoms, or mixtures thereof, and
  • the invention provides a method of preparing a ternary surfactant composition comprising combining (a) a cationic surfactant which is a quaternary ammonium compound of the formula
  • R R 2 , and R 3 are independently ethyl or methyl
  • R 4 is an alkyl group having an average of from about 8 to about 16 carbon atoms
  • X is halogen, sulfate, methosulfate, ethosulfate, tosylate, acetate, phosphate, nitrate, sulfonate, or carboxylate, and
  • (vn) a sarcosinate having an average of from about 10 to about 16 carbon atoms, or
  • a bridging surfactant selected from the group consisting of amine oxides, ethoxamides, and betaines, wherein the bridging surfactant is added first or second, and wherein the total concentration of combined cationic, anionic, and bridging surfactants is from about 30 to about 80 percent by weight, and wherein the surfactant blend is flowable
  • the invention provides a method for enhancing the solubility of an anionic- cationic surfactant complex comprising combining (a) an anionic-cationic complex formed by combining in any order
  • R-), R 2 , and R 3 are independently ethyl or methyl, R 4 is an alkyl group having an average of from about 8 to about 16 carbon atoms, and
  • X is halogen, sulfate, methosulfate, ethosulfate, tosylate, acetate, phosphate, nitrate, sulfonate, or carboxylate, and (II) an anionic surfactant which is
  • an alkyl ether sulfate having an average of from about 8 to about 16 carbon atoms in the alkyl portion and from about 1 to about 30 moles of ethylene oxide
  • a bridging surfactant selected from the group consisting of amine oxides, ethoxamides, and betaines
  • the invention provides surfactant blends comprising a synergistic mixture of anionic and cationic surfactants that are generally water soluble without the use of organic solvents or insertion of alkoxy chains into either the anionic or cationic surfactant
  • the invention further provides surfactant blends exhibiting excellent detergent properties comprising a synergistic mixture of anionic and cationic surfactants that are generally flowable at concentrations as high as about 80 percent by weight, and, when diluted to a concentration of about 0 1 percent by weight in water, generally form clear aqueous solutions substantially free of precipitates
  • Cationic and anionic surfactants form complexes that are generally insoluble because the charged heads (anionic or cationic) responsible for water solubility are neutralized during complexation
  • anionic surfactant and anionic surfactant are combined with a bridging surfactant to form a ternary blend, a substantially water-soluble system is produced
  • additional hydrophihc groups such as ethylene oxide groups or additional charge that remains un-neutra zed during complexation
  • the present invention provides ternary blends of cationic, anionic and bridging surfactants wherein anionic/cationic complexes are formed While not intending to be limited by a particular theory, it is believed that the quaternary ammonium agent (a cationic surfactant) and anionic surfactants typically form ion pair complexes in aqueous solutions
  • the ion pairs formed between tn-short chain, mono-long chain quaternary ammonium halides and many anionic surfactants have low solubility and precipitate as a solid salt at typical use concentrations This not only has a negative effect on cleaning performance, but also prevents use of such anionic-cationic ion pair complexes in isotropic liquid detergents
  • ion pairs formed by such cationic surfactants and many anionic surfactants in the presence of a bridging surfactant are much more soluble in bulk surfactant compositions, as detailed herein This increased solubility allows for greater flexibility in formulating with the bulk surfactant
  • anionic-cationic complex is solubilized within the ternary surfactant blends of the invention.
  • the interfacial surface tension and detergency behavior of an anionic-cationic complex is very different compared to either of the individual anionic and cationic surfactant components
  • an anionic- cationic complex exhibits significantly lower interfacial surface tension and significantly higher foaming than either an anionic or cationic surfactant alone
  • the interfacial tension between certain oils and an aqueous solution of a ternary surfactant blend of the invention was found to be lower than the interfacial tension between the same oils and an aqueous solution of the individual anionic, cationic, or bridging surfactants, or combinations of two of these surfactants.
  • ternary surfactant blends of this invention are generally provided in the form of a flowable composition that can be expected to be stored for long periods of time prior to sale or use
  • the formation of an anionic-cationic precipitate is avoided herein, and a lack of such a precipitate in the compositions of this invention is one of this invention's advantages
  • the invention provides methods for preparing ternary surfactant blends The ternary blends of the invention are readily obtained by merely pre-mixing either the anionic or the cationic surfactant with the bridging surfactant, followed by mixing with the surfactant not pre-mixed
  • the present invention provides complexes useful as rheology modifiers
  • the present invention further encompasses consumer detergent, laundry and personal care products prepared using the surfactant blends and/or complexes detailed herein
  • the essential, as well as the optional, components of the present invention are described below Cationic Surfactants
  • the cationic surfactant is a surfactant selected from the group comprising fatty amine salts, fatty diamine salts, polyamine salts, quaternary ammonium salts, polyoxyethyleneated fatty amine salts, quaternized polyoxyethyleneated fatty amines, and mixtures thereof
  • cationic surfactants useful in the present invention include those disclosed in the following documents, all of which are incorporated by reference herein M C Publishing Co , McCutcheon's Detergents & Emulsifiers, (North American Ed , 1993), Schwartz et al , Surface Active Agents, Their Chemistry and Technology, New York, Interscience Publisher, 1949, U S Pat No 3,155,591 , Spotifyr, issued Nov 3, 1964, U S Pat No 3,929,678, Laugh n et al , issued Dec 30, 1975, U S Pat No 3,959,461 , Bailey et al , issued May 25, 1976,
  • Salts of primary, secondary and tertiary fatty amines are also suitable cationic surfactant materials
  • the alkyl groups of such amine salts preferably have from about 12 to about 22 carbon atoms, and may be substituted or unsubstituted Secondary and tertiary amine salts are preferred, tertiary amine salts are particularly preferred Suitable amine salts include the halogen (i e fluoride, chloride, bromide), acetate, phosphate, nitrate, citrate, lactate and alkyl sulfate salts Amine salts derived from amine, such as for example, stearamido propyl dimethyl amine, diethyl ammo ethyl stearamide, dimethyl stearamine, dimethyl soyamine, soyamine, my ⁇ styl amine, tndecyl amine, ethyl stearylamine, N-tallowpropane diamine, ethoxyl
  • cationic surfactants particularly useful herein are those of the general formula
  • R ⁇ R 2 , and R 3 are independently ethyl or methyl
  • R 4 is an alkyl group having an average of from about 8 to about 16 carbon atoms
  • X is an a suitable ion including but not limited to halogen, sulfate, methosulfate, ethosulfate, tosylate, acetate, phosphate, nitrate, sulfonate, or carboxylate
  • quaternary ammonium compounds and amine salt compounds include those of the above general formula in the form of ring structures formed by covalently linking two of the radicals
  • examples include imidazolines, imidazoliniums, and py ⁇ diniums, etc , wherein said compound has at least one nonionic hydrophile-containing radical as set forth above
  • Specific examples include 2-heptadecyl-4,5- d ⁇ hydro-1 H- ⁇ m ⁇ dazol-1-ethanol, 4,5-d ⁇ hydro-1-(2-hydroxyethyl)-2- ⁇ soheptadecyl-1-phenylmethyl ⁇ m ⁇ dazol ⁇ um chloride, and 1-[2-oxo-2-[[2-[(1-oxoctadecyl)oxy]ethyl]am ⁇ no]ethyl] py ⁇ diniur ⁇ chloride
  • useful polymenzable surface active agents include those of the above general formula in the form of ring structures formed by covalently linking two of the
  • the most preferred cationic surfactants for use in the present invention include octylt ⁇ methyl ammonium chloride, decyltnmethyl ammonium chloride, dodecyltnmethyl ammonium bromide, dodecyltn methyl ammonium chloride, Cetac ® -30, BTC ® -65NF, BTC ® -835 and BTC ® -885, all commercially available from Stepan Company Anionic Surfactants
  • anionic surfactants that may be utilized according to the present invention are well known to the art and are described below in a representative manner Generally speaking, a variety of anionic surfactants useful in the present invention are well known in the art Anionic surfactants useful herein include those disclosed in the following documents, all of which are incorporated by reference herein M C Publishing Co , McCutcheon's Detergents & Emulsifiers, (North American Ed , 1993), Schwartz et al , Surface Active Agents, Their Chemistry and Technology, New York, Interscience Publisher, 1949, U S Pat No 4,285,841 , Barrat et al, issued Aug 25, 1981 , and U S Pat No 3,919,678, Laughlin et al, issued Dec 30, 1975
  • the anionic surfactants of the present invention generally include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, d ⁇ -, and t ⁇ ethanolamine salts) of the anionic sulfate, sulfonate, carboxylate and sarcosmate surfactants
  • suitable anionic surfactants include the isethionates such as the acyl isethionates, N-acyl taurates, fatty acid amides of methyl tau ⁇ de, alkyl succinates and sulfosuccinates, monoesters of sulfosuccinate (especially saturated and unsaturated C ⁇ 2 -C 18 monoesters), diesters of sulfosuccinate (especially saturated and unsaturated C 6 -C-i 4 diesters), and N-acyl sarcosinates
  • Resin acids and hydrogenated resin acids are also suitable, such as rosin, hydrogenated rosin, and resin acids and
  • Anionic sulfate surfactants suitable for use in the compositions of the invention include the linear and branched primary and secondary alkyl sulfates, alkyl ethoxysulfates, fatty oleyl glycerol sulfates, alkyl phenol ethoxylate sulfates, alkyl phenol ethylene oxide ether sulfates, the C 5 -C 17 acyl-N-(CrC 4 alkyl) and -
  • N-(C ! -C 2 hydroxyalkyl) glucamine sulfates and sulfates of alkylpolysacchandes such as the sulfates of alkylpolyglucoside
  • Alkyl sulfate surfactants are preferably selected from the group consisting of the C 8 -C 22 alkyl sulfates
  • the alkyl sulfate surfactant is a C 8 -C 16 alkyl sulfate
  • Alkyl ethoxysulfate surfactants are preferably selected from the group consisting of the C 8 -C 22 alkyl sulfates that have been ethoxylated with from about 0 5 to about 30 moles of ethylene oxide per molecule
  • the alkyl ethoxysulfate surfactant is a C 8 -C 16 alkyl sulfate which has been ethoxylated with from about 1 to about 30 moles of ethylene oxide
  • a particularly preferred aspect of the invention employs mixtures of C 8 alkyl sulfate (Polystep ® B-
  • Anionic sulfonate surfactant Anionic sulfonate surfactant
  • Anionic sulfonate surfactants suitable for use herein include the salts of C 5 -C 20 linear alkylbenzene sulfonates, alkyl ester sulfonates, C 6 -C 22 primary or secondary alkane sulfonates, C 6 -C 24 olefin sulfonates, alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleyl glycerol sulfonates, and any mixtures thereof
  • Anionic sulfonate surfactants are preferably selected from the group consisting of the C 8 -
  • the anionic sulfonate surfactant is an C 8 -C 18 alkyl sulfonate, such as Bioterge ® PAS-8S (commercially available from Stepan Company,
  • Suitable anionic carboxylate surfactants include the alkyl ethoxy carboxylates, the alkyl polyethoxy polycarboxylate surfactants and the soaps ("alkyl carboxyls"), especially certain secondary soaps as described herein
  • Suitable alkyl ethoxy carboxylates include those with the formula RO(CH 2 CH 2 0) x CH 2 COO M + wherein R is a C 6 to C 18 alkyl group, x ranges from 0 to 10, and the ethoxylate distribution is such that, on a weight basis, the amount of material where x is 0 is less than about 20 percent and M is a cation
  • Suitable alkyl polyethoxy polycarboxylate surfactants include those having the formula RO(CHR 1 CHR 2 0)R 3 wherein R is a C 6 to C 1 ⁇ alkyl group, x ranges from 1 to 25, Ri and R 2 are selected from the group consisting of hydrogen, methyl acid radical, succmic acid radical, hydroxysuccinic acid radical, and mixtures thereof, and R 3 is selected from the group consisting of hydrogen, substituted or unsubstituted hydrocarbon having between 1 and 8 carbon atoms, and mixtures thereof
  • Suitable soap surfactants include the secondary soap surfactants which contain a carboxyl unit connected to a secondary carbon
  • Preferred secondary soap surfactants for use herein are water-soluble members selected from the group consisting of the water-soluble salts of 2-methyl-1-undecano ⁇ c acid, 2- ethyl-1 -decanoic acid, 2-propyl-1 -nonanoic acid, 2-butyl-1 -octanoic acid and 2-pentyl-1 -heptanoic acid
  • Suitable anionic sulfosuccinates include those having the formula o o Q o
  • R and R(CH 2 CH 2 0) x where x has an average value from about 1 to about 30, R is C 8 -C 22 alkyl, and M is an alkali metal countenon
  • Anionic sulfosuccinate surfactants are preferably selected from the group consisting of the C 8 -C 22 sulfosuccinates Most preferably, the anionic sulfosuccinate surfactants is a r ⁇ ono-
  • C 10 -Ci 6 alkyl sulfosuccinate such as disodium laureth sulfosuccinate (Stepan-Mild ® SL3, commercially available from Stepan Company, Northfield, Illinois)
  • Anionic ⁇ -sulfonated methyl ester surfactant such as disodium laureth sulfosuccinate (Stepan-Mild ® SL3, commercially available from Stepan Company, Northfield, Illinois).
  • Suitable ⁇ -sulfonated methyl esters include those having the formula O O
  • X and Y are the same or different and are selected from the group consisting of C 8 -C 22 alkyl, and M is an alkali metal counte ⁇ on
  • Anionic ⁇ -sulfonated methyl ester surfactants are preferably selected from the group consisting of the ⁇ -sulfonated C C ⁇ alkyl esters of fatty acids having an average of from about 8 to about 22 carbon atoms
  • the anionic ⁇ -sulfonated methyl ester surfactants is selected from the group consisting of the ⁇ -sulfonated d-C 6 alkyl esters of fatty acids having an average of from about 11 to about 16 carbon atoms
  • the anionic ⁇ -sulfonated methyl ester surfactants is Alpha Step ® MC-48 or Alpha Step ® ML-40 (both commercially available from Stepan Company, Northfield, Illinois) Alkali metal sarcosinate surfactant
  • alkali metal sarcosinates of the formula RCON(R 1 )CH 2 COOM, wherein R is a C 5 -C 22 linear or branched alkyl or alkenyl group, R, is a C 1 -C 4 alkyl group and M is an alkali metal ion
  • R is a C 5 -C 22 linear or branched alkyl or alkenyl group
  • R is a C 1 -C 4 alkyl group
  • M is an alkali metal ion
  • Preferred alkali metal sarcosinate surfactants include but are not limited to the my ⁇ styl and oleoyl methyl sarcosinates in the form of their sodium salts
  • the alkali metal sarcosinate surfactant is a C 10 -C 16 sarcosinate such as Maprosyl ® 30 (commercially available from Stepan Company, Northfield, Illinois) Alkyl sulfoacetates
  • alkyl sulfoacetates of the formula RO(CO)CH 2 S0 3 M, wherein R is a C 12 -C 20 alkyl group and M is an alkali metal ion
  • Preferred alkyl sulfoacetates include but are not limited to the lauryl and my ⁇ styl sulfoacetates in the form of their sodium salts
  • the alkyl sulfoacetate is Lathanol ® LAL (commercially available from Stepan Company, Northfield, Illinois) Bridging Surfactants
  • the bridging surfactants of the present invention are selected from the group consisting of semi- polar nonionic, ethoxamide, and amphotenc surfactants and mixtures thereof Especially preferred bridging surfactants include amine oxides, ethoxylated alkanolamides, and betaines Semi-Polar Nonionic Surfactants
  • Semi-polar nonionic surfactants include water-soluble amine oxides having an alkyl moiety containing 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
  • Semi-polar nonionic surfactants also include water-soluble sulfoxides having alkyl moieties containing from about 10 to about 18 carbon atoms and a moiety selected from the group comprising alkyl groups and hydroxyalkyl groups of from about 1 to about 3 carbon atoms
  • the present invention encompasses semi-polar nonionic surfactants that are amine oxides formed as shown in Scheme I. wherein R ⁇ R 2 , R 3 independently are substituted or unsubstituted hydrocarbyl groups of from about 1 to about 30 carbon atoms, or hydrocarbyl groups having from about 1 to about 30 carbon atoms and containing one or more aromatic, ether, ester, amido, or ammo moieties present as substituents or as linkages in the radical chain, and wherein X is an anion group selected from the group consisting of halogen, sulfonate, sulfate, sulfinate, sulfenate, phosphate, carboxylate, nitrate, and acetate
  • useful semi-polar nonionic surfactants include those of the below general formula in the form of ring structures formed by covalently linking two of the R 1 -R 4 groups Examples include unsaturated imidazolines, imidazoliniums, and pyndiniums, and
  • Particularly preferred amine oxides include but are not limited to Ammonyx ® C8 (octylamine oxide), Ammonyx ® C10 (decylamine oxide), Ammonyx ® LO (laurylamine oxide), Ammonyx ® MO (my ⁇ stylamine oxide), Ammonyx ® MCO (my ⁇ styl/cetylamine oxide), and Ammonyx ® CDO (cocamidoproylamine oxide), all commercially available from Stepan Company, Northfield, Illinois Ethoxamides
  • Ethoxamides also termed ethoxylated alkanolamides or polyethylene glycol amides
  • Ethoxamides include those having the formula
  • RCO- represents the fatty acids derived from coconut oil, m is an integer from about 8 to about 16, n has an average value of about 3,
  • Y is hydrogen or (CH 2 CH 2 0) p H; and p is 0, 1 or more Preferred ethoxamides include but are not limited to Amidox ® C-2 (PEG-3 cocamide), Amidox ® C-5 (PEG- 6 cocamide), and Amidox ® L-5 (PEG-6 lauramide), all commercially available from Stepan Company, Northfield, Illinois
  • Suitable amphote ⁇ c surfactants are selected from the group consisting of alkyl glycmates, propionates, imidazolines, amphoalkylsulfonates (sold under the tradename Miranol® by Rhone Poulenc),
  • N-alkylaminopropionic acids N-alkyliminodipropiomc acids, imidazolme carboxy-lates, N-alkylbetaines, amido propyl betaines, sarcosinates, cocoamphocarboxyglycmates, amine oxides, sulfobetames, sultaines and mixtures thereof
  • Additional suitable amphotenc surfactants include cocoamphoglycinate, cocoamphocarboxyglycinate, lauramphocarboxyglycinate, coco-amphopropionate, lauramphopropionate, stearamphoglycinate, cocoamphocarboxypropionate, tallowamphopropionate, tallowamphoglycinate, oleoamphoglycinate, caproamphoglycmate, caprylamphopropionate, caprylamphocarboxyglycinate, cocoyl imidazolme, lauryl imidazolme, stearyl
  • betaines and sultaines which are suitable for use as bridging surfactants are alkyl betaines and sultaines sold under the tradename Miratame ® by Rhone Poulenc, and Lonzaine ® by Lonza, Inc , Fairlawn, N J Additional examples of betaines and sultaines include cocobetaine, cocoamidoethyl betaine, cocoamidopropyl betame, lauryl betame, lauramidopropyl betame, palmamidopropyl betame, stearamidopropyl betaine, stearyl betaine, cocosultame, lauryl sultame, tallowamidopropyl hydroxysultame and the like Particularly preferred amphotenc surfactants include Amphosol ® CA (cocamidopropyl betaine) and Amphosol ® DM (lauryl betaine), both commercially available from Stepan Company, Northfield, Illinois Optional Ingredients
  • the ternary surfactant blends may be formulated with optional components, such as fragrances, emollient, solvents, humectants, optical bnghtners, thickeners, powders, viscosity modifiers, hydrotropes, preservatives, bluing agents, and dyes, to produce a wide variety of end use products
  • optional components such as fragrances, emollient, solvents, humectants, optical bnghtners, thickeners, powders, viscosity modifiers, hydrotropes, preservatives, bluing agents, and dyes
  • suitable optional emollients useful in formulating with blends of the present invention include, for example, stearyl alcohol, glyceryl ncinoleate, glyceryl stearate, propane-1 ,2-d ⁇ ol, butane-1 ,3-d ⁇ ol, mink oil, cetyl alcohol, stearamidopropyl dimethylamme, isopropyl isostearate, steanc acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone oils such as dimethylpolysiloxane, dimethicone
  • Optional powders useful in formulating with blends of the present invention include, for example, chalk, talc, fullers earth, kaolin, starch, gums, colloidal silicon dioxide, sodium polyacrylate, tetra alkyl and/or tnalkyl aryl ammonium smectites, chemically modified magnesium aluminum silicate, organically modified montmorillonite clay, hydrated aluminum silicate, fumed silica, carboxyvinyl polymer, cellulosics such as hydroxyethyl cellulose and sodium carboxymethyl cellulose, ethylene glycol monostearate, zinc or magnesium stearate, zinc oxide and magnesium oxide, and mixtures thereof These components may also be used as thickeners in fluid or semi-fluid compositions
  • Examples of other optional ingredients useful in formulating with blends of the present invention include, for example, volatile and non-volatile si cones, silicone polymers, preservatives, such as para- hydroxy benzoate esters, humectants, such as butan
  • the blends of the present invention may also be formulated with optional detergent builder materials
  • any detergent builders known in the art can be formulated with the present blends
  • useful detergent builders are described in U S Pat Nos 4,321 ,165, (to Smith et al, issued Mar 23, 1982) and 5,565,145 (to Watson et al , issued Oct 15, 1996), both incorporated herein by reference
  • Detergent builders can optionally be included in the compositions herein to assist in controlling mineral hardness Inorganic as well as organic builders can be used
  • Builders are typically used in fabric laundering compositions to assist in the removal of particulate soils
  • the level of builder can vary widely depending upon the end use of the composition and its desired physical form When present in a final formulation, the compositions will typically comprise at least about 1% builder Liquid formulations typically comprise from about 5% to about 50%, more typically about 5% to about 30%, by weight, of detergent builder Granular finished formulations typically comprise from about 10% to about 80%, more typically from about 15% to about 50% by weight
  • Enzymes and enzyme stabilizers can be formulated with blends of the instant invention for a wide variety of fabric laundering purposes, including removal of protein-based, carbohydrate-based, or triglycende-based stains, for example, and for fabric restoration
  • useful enzymes and enzyme stabilizers are described in U S Pat No 5,565,145 (to Watson et al , issued Oct 15, 1996), incorporated herein by reference
  • Useful enzymes include, for example, proteases, amylases, lipases, and cellulases, as well as mixtures thereof Other types of enzymes may also be included They may be of any suitable origin, such as vegetable, animal, bacterial, fungal and yeast origin However, a particular enzyme choice is governed by several factors such as pH-activity and/or stability optima, thermostability, stability versus active detergents, builders and so on In this respect bacterial or fungal enzymes are preferred, such as bacterial amylases and proteases, and fungal cellulases
  • proteases are the subtilisms which are obtained from particular strains of B subti s and B licheniforms
  • Another suitable protease is obtained from a strain of Bacillus, having maximum activity throughout the pH range of 8-12, developed and sold by Novo Industries A/S under the registered trade name ESPERASE
  • Other proteases include Protease A (see European Patent Application 130,756, published Jan 9, 1985) and Protease B (see European Patent Application Ser No 87303761 8, filed Apr 28, 1987, and European Patent Application 130,756, Bott et al, published Jan 9, 1985)
  • Amylases include, for example, -amylases described in British Patent Specification No 1 ,296,839 (Novo), RAPIDASE, International Bio-Synthetics, Inc and TERMAMYL, Novo Industries
  • Cellulases suitable for use with ternary surfactant blends of the present invention include both bacte ⁇ al or fungal cellulase Preferably, they will have a pH optimum of between 5 and 9 5
  • Suitable cellulases are disclosed in U S Pat 4,435,307, Barbesgoard et al, issued Mar 6, 1984, which discloses fungal cellulase produced from Humicola insolens and Humicola strain DSM1800 or a cellulase 212- producing fungus belonging to the genus Aeromonas, and cellulase extracted from the hepatopancreas of a marine mollusk (Dolabella Auricula Solander) Suitable cellulases are also disclosed in GB-A-2
  • Suitable lipase enzymes include those produced by microorganisms of the Pseudomonas group, such as Pseudomonas stutze ⁇ ATCC 19.154, as disclosed in British Patent 1 ,372,034 See also lipases in Japanese Patent Application 53,20487, laid open to public inspection on Feb 24, 1978 This lipase is available from Amano Pharmaceutical Co Ltd , Nagoya, Japan, under the trade name Lipase P Amano, hereinafter referred to as Amano-P Other commercial lipases include Amano-CES, lipases ex Chromobacter viscosum, e g Chromobacter viscosum var lipolyticum NRRLB 3673, commercially available from Toyo Jozo Co , Tagata, Japan, and further Chromobacter viscosum lipases from U S Biochemical Corp , U S A and Diosynth Co , The Netherlands, and lipases ex Pseudomonas gladioli The LIPOLASE enzyme
  • final formulations prepared from the blends disclosed herein typically will comprise from about 0 05% to about 2% by weight of a water-soluble source of calcium or magnesium ions, or both
  • the amount of water- soluble ion can vary with the amount and type of enzyme employed in the final composition
  • Final compositions based on the blends detailed herein may also optionally contain various additional stabilizers, especially borate-type stabilizers Boric acid is preferred, although other compounds such as boric oxide, borax and other alkali metal borates (e g , sodium ortho-, meta- and pyroborate, and sodium pentaborate) are suitable
  • Substituted boric acids e g , phenylboronic acid, butane boronic acid, and p-bromo phenylboronic acid
  • Bleaching agents, bleach activators, chelatmg agents, anti-redeposition agents, polymeric dispersing agents, optical b ⁇ ghteners, suds suppressors, dye transfer inhibition agents, optical b ⁇ ghteners, and soil release agents can be formulated with blends of the instant invention Examples of such materials are generally described in U S Pat No 5,565,145 (to Watson et al , issued Oct 15, 1996), incorporated herein by reference
  • detergent additives or adjuvants may be present in the detergent product to give it additional desired properties, either of functional or aesthetic nature
  • minor amounts of soil suspending or anti-redeposition agents e g polyvmyl alcohol, fatty amides, sodium carboxymethyl cellulose, hydroxy-propyl methyl cellulose, optical bnghteners, e g cotton, amine and polyester bnghteners, for example, stilbene, tnazole and benzid e sulfone compositions, especially, sulfonated substituted tnazinyl stilbene, sulfonated naphthot ⁇ azole stilbene, benzidme sulfone, etc , most preferred are stilbene and tnazole combinations Bluing agents such as ultramarine blue, enzymes, preferably proteolytic enzymes, such as subtilism, bromelm, papam, trypsm and pepsin, as well as amylase type enzymes,
  • C22 alkyl alcohol with C12 to C-13 alkylsulfate, pH modifiers and pH buffers, color safe bleaches, perfume and anti-foam agents or suds suppressors, e g silicon compounds, can also be used
  • other optional ingredients include neutralizing agents, buffering agents, phase regulants, hydrotropes, polyacids, suds regulants, opacifiers, antioxidants, preservatives, bacte ⁇ cides, dyes, perfumes, and bnghteners described in the U S Pat No 4,285,841 , Barrat et al, issued Aug 25, 1981 , incorporated herein by reference
  • Other ingredients useful in final detergent compositions can be formulated with blends of the instant invention, including carders, processing aids, pigments, solvents for liquid formulations, solid fillers for bar compositions, sodium sulfate, sodium chloride, protein hydrolysates, cholesterol derivatives, UV absorbers, chelatmg agents, etc
  • suds boosters such as the C-
  • the ternary surfactant blends of the present invention typically are prepared having a pH of between about 2 and about 10, preferably between about 5 and about 8 Techniques for controlling pH at recommended usage levels include the use of buffers, alkalis, acids, etc , and are well known to those skilled in the art Suitable materials for adjusting the pH of these compositions include triethanolamme, diethanolamine, sodium carbonate, sodium bicarbonate, and the
  • Ternary surfactant blends of this invention may be formulated into commercially useful products having an active level of cationic, anionic and bridging surfactants combined of from about 0 1 to about 98 percent by weight solids More typically, ternary surfactant blends of the present invention are flowable and have a total surfactant concentration of from about 5 to about 80 percent by weight of the composition Ternary surfactant blends of the invention are preferably clear and exhibit no precipitate formation upon aging Additionally, the ternary surfactant blends may be processed into a variety of forms such as, for example, liquids, solutions, solids, powders, flakes, semi-solids, gels, "ringing" gels, G- phase liquids/pastes, hexagonal liquid crystal phases, or thick non-flowable pastes The ternary surfactant blends may be spray dried, flaked, or extruded Although not critical to the present invention, the blends may be prepared "neat” or in a conventional solvent such as water, low molecular weight alcohol or hydro
  • Maprosyl ® 30 Sodium lauroyl sarcosinate (commercially available from Stepan Company, Northfield Illinois)
  • Stepan-Mild ® SL3 Disodium laureth sulfosuccinate (commercially available from Stepan Company, Northfield Illinois)
  • Stepanol ® WA-Extra Sodium lauryl sulfate (commercially available from Stepan Company, Northfield Illinois)
  • Bioterge ® AS-40 Sodium C14-16 olefin sulfonate (commercially available from Stepan Company, Northfield Illinois)
  • Cetac ® 30 Cetylt ⁇ methylammonium chloride (commercially available from Stepan Company, Northfield Illinois)
  • Ammonyx ® LO Lauramme oxide (commercially available from Stepan Company, Northfield Illinois)
  • Ammonyx ® MCO My ⁇ styl/cetyl amine oxide (commercially available from Stepan Company, Northfield Illinois)
  • Ammonyx ® C8 Octylamine oxide (commercially available from Stepan Company, Northfield Illinois)
  • Amphosol ® DM Lauryl betaine (commercially available from Stepan Company, Northfield Illinois)
  • Amidox ® C-2 PEG-3 Cocamide commercially available from Stepan Company, Northfield Illinois
  • a ternary surfactant blend of an anionic surfactant, a cationic surfactant, and a bridging surfactant was prepared by mixing at room temperature equal moles of Alpha Step ® ML-40, QC10, and Amphosol ® CA. A 33.03% clear liquid phase free of precipitate was obtained.
  • This surfactant blend displayed remarkable synergism, as shown in Table II, which shows that the ternary surfactant blend possesses surface tension, wetting, and foaming properties all dramatically better than the properties of any single surfactant or combination of two surfactants.
  • ternary surfactant blends as shown in Table III were prepared by mixing at room temperature equal moles of an anionic surfactant, a cationic surfactant, and a bridging surfactant. Appearance, surface tension, wetting, and foaming properties were evaluated for each blend over a range of pH. For the systems tested, when a betaine is used as the bridging surfactant, clarity can be maintained over a wide pH range. When an amine oxide is used as the bridging surfactant, clarity can be maintained when pH is above about 7.
  • ternary surfactant blends as shown in Table IV were prepared by mixing at room temperature equal moles of an anionic surfactant, a cationic surfactant, and a bridging surfactant. Appearance, surface tension, wetting, and foaming properties were evaluated for each blend. The results indicate that when magnesium ions are added to the ternary surfactant blends, the clarity and surfactant properties of the mixture are maintained.
  • ternary surfactant blends as shown in Table V were prepared by mixing at room temperature equal moles of an anionic surfactant, a cationic surfactant, and a bridging surfactant. Surface tension, wetting, and foaming properties were evaluated for each blend. The results indicate that surfactant properties of the ternary blends can be tailored by altering the identity of the bridging surfactant, or the chain length of the anionic and/or cationic surfactant. For example, increasing the chain length of the cationic surfactant decreases wetting time (12 seconds, compared to 5 seconds). Furthermore, increasing the chain length of the anionic surfactant also decreases wetting time (7 seconds, as compared to 3 seconds). Finally, changing the bridging surfactant from an amine oxide to a betaine increases foaming (14.7 cm., compared to 17.3 cm.).
  • ternary surfactant blends as shown in Table VI were prepared by mixing at room temperature equal moles of an anionic surfactant, a cationic surfactant, and a bridging surfactant. Appearance, surface tension, wetting, and foaming properties were evaluated for each blend. The results indicate that clarity and surfactant properties of the ternary blends of the invention can be maintained for a range of anionic, cationic, and bridging surfactants.

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Abstract

L'invention concerne des mélanges de tensioactifs ternaires comprenant au moins un tensioactif cationique, au moins un tensioactif anionique et au moins un « tensioactif de pontage » sélectionné dans les tensioactifs semi-polaires non ioniques, alcynolamides éthoxylés, et amphotériques/zwitterioniques, et des mélanges de ceux-ci. De manière plus spécifique, l'invention concerne des mélanges synergiques stables de tensioactifs cationiques, anioniques et de tensioactifs de pontage, qui sont utiles en tant que mélanges de tensioactifs en vrac. Ces mélanges de tensioactifs conviennent pour la préparation de divers produits de nettoyage finis destinés à la consommation, notamment des détergents de vaisselle liquides, des détergents de lessive, des détergents de lave-vaisselle, des savons pour les mains, des pains de lessive, des pains de toilette, des produits de nettoyage universels, des shampooings multi fonctionnels, des gels douche et des compositions de traitement de textiles. Ces mélanges de tensioactifs conviennent également pour les applications de l'agriculture et des pesticides. Ils peuvent en outre être utilisés dans des formulations détergentes anti-microbiennes (p. ex. nettoyants antimicrobiens pour surfaces dures, savons à main, shampooings et détergents de vaisselle), dans des systèmes vecteurs de détergents doux et dans des compositions de prétraitement des taches.
PCT/US2000/023719 1999-09-17 2000-08-29 Melanges de tensioactifs ternaires comprenant des tensioactifs cationiques, anioniques et des tensioactifs de pontage et procedes de preparation de ces melanges WO2001019507A1 (fr)

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AU69453/00A AU6945300A (en) 1999-09-17 2000-08-29 Ternary surfactant blends comprising cationic, anionic, and bridging surfactantsand methods of preparing same
CA002397811A CA2397811A1 (fr) 1999-09-17 2000-08-29 Melanges de tensioactifs ternaires comprenant des tensioactifs cationiques, anioniques et des tensioactifs de pontage et procedes de preparation de ces melanges
EP00957899A EP1257350A1 (fr) 1999-09-17 2000-08-29 Melanges de tensioactifs ternaires comprenant des tensioactifs cationiques, anioniques et des tensioactifs de pontage et procedes de preparation de ces melanges

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WO2007117720A2 (fr) * 2006-04-05 2007-10-18 Elc Management Llc Agents hydrophobes formant une dispersion stable dans des emulsions huile dans eau
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WO2002022083A3 (fr) * 2000-09-15 2002-06-13 Stepan Co Emulsion comprenant un melange ternaire de tensioactifs de pontage, cationiques et anioniques, d'huile et d'eau, et procede de preparation de cette emulsion
WO2002022105A3 (fr) * 2000-09-15 2002-07-11 Stepan Co Composition a effet de shampooing et savon liquide pour le corps comportant des melanges tensioactifs ternaires d'agents tensioactifs cationiques, anioniques et de pontage et procede de preparation de ladite composition
WO2002022105A2 (fr) * 2000-09-15 2002-03-21 Stepan Company Composition a effet de shampooing et savon liquide pour le corps comportant des melanges tensioactifs ternaires d'agents tensioactifs cationiques, anioniques et de pontage et procede de preparation de ladite composition
EP1377255A4 (fr) * 2001-03-30 2008-11-19 Color Access Inc Nouvelles nanoemulsions
EP1377255A1 (fr) * 2001-03-30 2004-01-07 Color Access, Inc. Nouvelles nanoemulsions
US7363978B2 (en) 2005-05-20 2008-04-29 Halliburton Energy Services, Inc. Methods of using reactive surfactants in subterranean operations
US8653010B2 (en) 2005-05-20 2014-02-18 Halliburton Energy Services, Inc. Methods of using reactive surfactants in subterranean operations
EP1757674A1 (fr) * 2005-08-27 2007-02-28 Clariant Produkte (Deutschland) GmbH Compositions adoucissantes pour tissus
WO2007025657A1 (fr) * 2005-08-27 2007-03-08 Clariant Produkte (Deutschland) Gmbh Composition adoucissante pour tissu
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WO2007064756A1 (fr) * 2005-11-29 2007-06-07 The Procter & Gamble Company Procédé de fabrication d'un liquide ionique comprenant des principes actifs ioniques
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WO2007117720A3 (fr) * 2006-04-05 2007-11-29 Elc Man Llc Agents hydrophobes formant une dispersion stable dans des emulsions huile dans eau
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