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EP0572723A1 - Compositions détergentes liquides structurées - Google Patents

Compositions détergentes liquides structurées Download PDF

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Publication number
EP0572723A1
EP0572723A1 EP92201567A EP92201567A EP0572723A1 EP 0572723 A1 EP0572723 A1 EP 0572723A1 EP 92201567 A EP92201567 A EP 92201567A EP 92201567 A EP92201567 A EP 92201567A EP 0572723 A1 EP0572723 A1 EP 0572723A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
composition according
surfactant
fatty acid
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP92201567A
Other languages
German (de)
English (en)
Inventor
Jean-Pol Boutique
Athanasios Surutzidis, (Nmn)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to EP92201567A priority Critical patent/EP0572723A1/fr
Priority to AU42339/93A priority patent/AU4233993A/en
Priority to CA 2136947 priority patent/CA2136947A1/fr
Priority to JP6500549A priority patent/JPH07507341A/ja
Priority to PCT/US1993/004232 priority patent/WO1993024602A1/fr
Priority to TR00413/93A priority patent/TR26929A/xx
Priority to IE930417A priority patent/IE930417A1/en
Priority to CN 93106573 priority patent/CN1079507A/zh
Publication of EP0572723A1 publication Critical patent/EP0572723A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
    • 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
    • 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
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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

Definitions

  • the present invention relates to structured liquid detergent compositions.
  • the compositions according to the present invention are especially suitable for suspending solid particles which are insoluble in the composition or liquids which are immiscible in the detergent composition.
  • the compositions according to this invention are particularly suitable for laundry applications.
  • Structured liquid detergents have been extensively described in the art, with a view to suspend solid particles which are insoluble in the detergent matrix, or liquids which are immiscible in the detergent matrix.
  • the presence of such ingredients generally leads to sedimentation or phase separation and therefore renders such detergents unacceptable from a consumer's viewpoint.
  • detergent formulators have designed structured liquid detergents which have the capability of stably suspending solids or immiscible liquids.
  • a typical approach to these compositions is the combination of an anionic surfactant with an electrolyte.
  • the electrolyte serves no other purpose than the formation of the suspending structure.
  • EP 414 549 to Albright & Wilson, discloses structured liquid compositions which are free of electrolyte. The structure is obtained by using particular surface-active systems which are quite unusual in the field of laundry detergents. No laundry cleaning composition is exemplified in EP 414 549.
  • EP 295 021 to Albright & Wilson, discloses a structured liquid surfactant system for use in liquid compositions, comprising an anionic surfactant and a highly hydrophobic nonionic surfactant.
  • an aqueous composition which comprises a mixture of an anionic surfactant and a hydrophilic polyhydroxy fatty acid amide surfactant.
  • Such polyhydroxy fatty acid amide surfactants have been described in laundry detergent compositions for instance in EP 285 758 and our co-pending applications PCT/US 91/07021, PCT/US 91/07025, PCT/US 91/07026, PCT/US 91/07027, PCT/US 91/07030 and PCT/US 91/06982.
  • compositions according to the present invention are aqueous liquid detergent compositions which comprise an anisotropic surfactant phase, comprising from 8% to 60% by weight of the total composition of a mixture of an anionic surfactant and a nonionic surfactant, characterized in that the nonionic surfactant is a polyhydroxy fatty acid amide of the formula: wherein R1 is H, a C1-C4 hydrocarbyl, 2-hydroxyethyl, 2-hydroxy propyl, or a mixture thereof, R2 is C5-C31 hydrocarbyl and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain, or an alkoxylated derivative thereof, and the weight ratio of said anionic surfactant to said polyhydroxy fatty acid amide nonionic surfactant is in the range of from 10:1 to 1:10.
  • compositions according to the present invention are aqueous structured compositions which comprise an anisotropic surfactant phase.
  • the presence of an anisotropic surfactant phase can be readily checked by observing a sample of the composition through an optical microscope, between Nichol prisms.
  • the anisotropic surfactant phase is formed by using a mixture of an anionic surfactant and a polyhydroxy fatty acid amide nonionic surfactant.
  • the compositions according to the present invention comprise from 8% to 60% by weight of the total composition of said surfactant mixture, preferably from 15% to 40%.
  • the polyhydroxyfatty acid amide nonionic surfactant suitable for use herein is of the formula: wherein: R1 is H, a 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 C5-C31 hydrocarbyl, preferably straight chain C7-C19 alkyl or alkenyl, more preferably straight chain C9-C17 alkyl or alkenyl, most preferably straight chain C11-C17 alkyl or alkenyl, or mixtures 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.
  • 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.
  • R1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
  • R2-CO-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-deoxymalto-triotityl, etc.
  • polyhydroxy fatty acid amides are known in the art. In general, they can be made by reacting an alkyl amine with a reducing sugar in a reductive amination reaction to form a corresponding N-alkyl polyhydroxyamine, and then reacting the N-alkyl polyhydroxyamine with a fatty aliphatic ester or triglyceride in a condensation/amidation step to form the N-alkyl, N-polyhydroxy fatty acid amide product.
  • Processes for making compositions containing polyhydroxy fatty acid amides are disclosed, for example, in G.B. Patent Specification 809,060, published February 18, 1959, by Thomas Hedley & Co., Ltd.; U.S.
  • N-deoxyglycityl fatty acid amides wherein the glycityl component is derived from glucose and the N-alkyl or N-hydroxyalkyl functionality is N-methyl, N-ethyl, N-propyl, N-butyl, N-hydroxyethyl, or N-hydroxypropyl
  • the product is made by reacting N-alkyl- or N-hydroxyalkyl-glucamine with a fatty ester selected from fatty methyl esters, fatty ethyl esters, and fatty triglycerides in the presence of a catalyst selected from the group consisting of trilithium phosphate, trisodium phosphate, tripotassium phosphate, tetrasodium pyrophosphate, pentapotassium tripholyphosphate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate,
  • the amount of catalyst is preferably from about 0.5 mole % to about 50 mole %, more preferably from about 2.0 mole % to about 10 mole %, on an N-alkyl or N-hydroxyalkyl-glucamine molar basis.
  • the reaction is preferably carried out at from about 138°C to about 170°C for typically from about 20 to about 90 minutes.
  • the reaction is also preferably carried out using from about 1 to about 10 weight % of a phase transfer agent, calculated on a weight percent basis of total reaction mixture, selected from saturated fatty alcohol polyethoxylates , alkylpolyglycosides , linear glycamide surfactant, and mixtures thereof.
  • a phase transfer agent calculated on a weight percent basis of total reaction mixture, selected from saturated fatty alcohol polyethoxylates , alkylpolyglycosides , linear glycamide surfactant, and mixtures thereof.
  • this process is carried out as follows:
  • N-linear glucosyl fatty acid amide product is added to the reaction mixture, by weight of the reactants, as the phase transfer agent if the fatty ester is a triglyceride. This seeds the reaction, thereby increasing reaction rate.
  • a detailed experimental procedure is provided below in the Experimental.
  • polyhydroxy "fatty acid” amide materials used herein also offer the advantages to the detergent formulator that they can be prepared wholly or primarily from natural, renewable, non-petrochemical feedstocks and are degradable. They also exhibit low toxicity to aquatic life.
  • the processes used to produce them will also typically produce quantities of nonvolatile by-product such as esteramides and cyclic polyhydroxy fatty acid amide.
  • the level of these by-products will vary depending upon the particular reactants and process conditions.
  • the polyhydroxy fatty acid amide incorporated into the detergent compositions hereof will be provided in a form such that the polyhydroxy fatty acid amide-containing composition added to the detergent contains less than about 10%, preferably less than about 4%, of cyclic polyhydroxy fatty acid amide.
  • the preferred processes described above are advantageous in that they can yield rather low levels of by-products, including such cyclic amide by-product.
  • alkyl benzene sulphonates The alkyl benzene sulfonate surfactants hereof are well known in the art. These surfactants have C9 and higher alkyl groups, preferably the alkyl groups are C9-C18 alkyl groups, more preferably linear, to provide the linear alkyl benzene sulfonate ("LAS") class of commercial surfactants. Especially preferred are C10-C14 LAS surfactant. These surfactants can be used in either the acid or soluble salt form. Suitable salts include metal salts (e.g., sodium, potassium, and lithium) as well as substituted and unsubstituted ammonium salts (e.g., ethanolamines).
  • metal salts e.g., sodium, potassium, and lithium
  • substituted and unsubstituted ammonium salts e.g., ethanolamines.
  • alkyl sulfate surfactants include water soluble salts or acids of the formula ROSO3M wherein R preferably is a C10-C24 hydrocarbyl, preferably branched, preferably an alkyl or hydroxyalkyl having a C10-C20 alkyl component, more preferably a C12-C18 alkyl or hydroxyalkyl, and M is a H or a cation, e.g., an alkali metal cation (e.g., sodium, potassium, lithium), substituted or unsubstituted ammonium cations such as methyl-, dimethyl-, and trimethyl ammonium cations and quaternary ammonium, e.g., tetramethyl-ammonium and dimethyl piperidinium, and cations derived from alkanolamines such as ethanolamine, diethanolamine, triethanolamine, and mixtures thereof, and the like.
  • Alkyl sulfate surfactants include water soluble salt
  • anionic surfactants useful for use herein include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of soap, C8-C22 primary or secondary alkanesulphonates, C8-C24 olefinsulphonates, sulphonated polycarboxylic acids prepared by sulphonation of the pyrolyzed product of alkaline earth metal citrates, e.g., as described in British patent specification No.
  • salts including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts
  • C8-C22 primary or secondary alkanesulphonates C8-C24 olefinsulphonates
  • sulphonated polycarboxylic acids prepared by sulphonation of the pyrolyzed product of alkaline earth metal citrates, e.g., as described in British patent specification No.
  • alkyl glycerol sulfonates 1,082,179, alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleyl glycerol sulfates, alkyl phenol ethylene oxide ether sulfates, sulfonates, alkyl phosphates, isethionates such as the acyl isethionates, N-acyl taurates, fatty acid amides of methyl tauride, alkyl succinamates and sulfosuccinates, monoesters of sulfosuccinate (especially saturated and unsaturated C12-C18 monoesters), diesters of sulfosuccinates (especially C6-C14 diesters), N-acyl sarcosinates, sulfates of alkyl-polysaccharides such as the sulfates of alkylpolyglucoside (
  • Resin acids and hydrogenated resin acids are also suitable, such as rosin, hydrogenated rosin, and resin acids and hydrogenated resin acids present in or derived from tall oil. Further examples are described in " Surface Active Agents and Detergents" (Vol. I and II by Schwartz, Perry and Berch). A variety of such surfactants are also generally disclosed in U.S. Patent 3,929,678, issued December 30, 1975 to Laughlin, et al, at Column 23, line 58 through Column 29, line 23 (herein incorporated by reference).
  • Preferred anionic surfactants for use herein are linear alkyl benzene sulfonates and alkyl sulfates, particularly linear alkyl benzene sulfonates.
  • the weight ratio of said anionic surfactant to said polyhydroxy fatty acid amide nonionic surfactant is in the range of from 10:1 to 1:10, preferably from 3:1 to 1:3.
  • compositions according to the present invention need no electrolyte to form the anisotropic phase. Accordingly, the compositions herein are substantially free of electrolyte.
  • electrolyte it is meant herein any material which has the sole function of building the anisotropic phase. It excludes other materials which may be regarded as electrolytes, but which provide detergency benefits, like citric acid, for instance.
  • the compositions according to the present invention can include from 2% to 20% by weight of the total composition, preferably from 8% to 15% of fatty acids.
  • Suitable fatty acids for use herein are fatty acids containing from 10 to 22 carbon atoms.
  • the fatty acids can also comprise from 1 to 10 ethylene oxide units in the hydrocarbon chain.
  • Preferred are fatty acids containing from about 12 to 14 carbon atoms.
  • compositions according to the present invention can also comprise additional surfactants which are well known to the man skilled in the art, other than the anionic and polyhydroxy fatty acid amide nonionic surfactants described hereinbefore, including cationic and zwitterionic surfactants.
  • additional surfactants which are well known to the man skilled in the art, other than the anionic and polyhydroxy fatty acid amide nonionic surfactants described hereinbefore, including cationic and zwitterionic surfactants.
  • the compositions according to the present invention may also comprise other nonionic surfactants than the polyhydroxy fatty acid amides described hereinbefore, including ethoxylated alcohols.
  • compositions according to the present invention may further comprise optional ingredients, depending on the use intended for said formulations.
  • optional ingredients include builders such as polyphosphates and phosphonates, zeolites and polycarboxylates, including citrates and succinates.
  • Further optionals include enzymes, including cellulases, proteases, lipases, amylases and peroxidases, as well as various enzyme stabilization systems.
  • Yet further ingredients include soil release agents, anti-redeposition agents, chelating agents, suds suppressors and solvents.
  • compositions according to the present invention are preferably formulated at a pH of from 6 to 9, preferably from 7 to 8.5.
  • compositions according to the present invention are particularly suitable for the purpose of suspending solid ingredients which are insoluble in the detergent matrix.
  • solid ingredients include for instance bleach particles such as perborate or percarbonate salts, or builder particles such as zeolite and citric acid; or high molecular weight polymers.
  • the compositions according to the present invention are also suitable for suspending liquids which are immiscible in the detergent matrix, for instance antifoam silicone oils, silicone/silica-based matrices and waxes.
  • compositions are made by mixing the listed ingredients in the listed proportions (weight %).

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Detergent Compositions (AREA)
EP92201567A 1992-06-02 1992-06-02 Compositions détergentes liquides structurées Withdrawn EP0572723A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP92201567A EP0572723A1 (fr) 1992-06-02 1992-06-02 Compositions détergentes liquides structurées
AU42339/93A AU4233993A (en) 1992-06-02 1993-05-05 Structured liquid detergent compositions
CA 2136947 CA2136947A1 (fr) 1992-06-02 1993-05-05 Compositions de detergent liquide structurees
JP6500549A JPH07507341A (ja) 1992-06-02 1993-05-05 構造化液体洗剤組成物
PCT/US1993/004232 WO1993024602A1 (fr) 1992-06-02 1993-05-05 Compositions detergentes liquides structurees
TR00413/93A TR26929A (tr) 1992-06-02 1993-05-24 Bir anizotropik yüzey aktif cismi fazi iceren sulu deterjan bilesimleri.
IE930417A IE930417A1 (en) 1992-06-02 1993-06-01 Structured liquid detergent compositions
CN 93106573 CN1079507A (zh) 1992-06-02 1993-06-02 结构性液体洗涤剂组合物

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP92201567A EP0572723A1 (fr) 1992-06-02 1992-06-02 Compositions détergentes liquides structurées

Publications (1)

Publication Number Publication Date
EP0572723A1 true EP0572723A1 (fr) 1993-12-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP92201567A Withdrawn EP0572723A1 (fr) 1992-06-02 1992-06-02 Compositions détergentes liquides structurées

Country Status (8)

Country Link
EP (1) EP0572723A1 (fr)
JP (1) JPH07507341A (fr)
CN (1) CN1079507A (fr)
AU (1) AU4233993A (fr)
CA (1) CA2136947A1 (fr)
IE (1) IE930417A1 (fr)
TR (1) TR26929A (fr)
WO (1) WO1993024602A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0675194A1 (fr) * 1994-03-28 1995-10-04 The Procter & Gamble Company Additifs pour détergents dans des liquides structurés
WO1996002620A1 (fr) * 1994-07-19 1996-02-01 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents a pouvoir ameliore de lavage
EP0738778A1 (fr) * 1995-04-19 1996-10-23 The Procter & Gamble Company Compositions détergentes non-aqueuses liquides contenant des particules
WO2009060312A3 (fr) * 2007-08-17 2009-11-05 Rhodia Asia Pacific Pte, Limited Compositions de savon structuré
JP2016517852A (ja) * 2013-04-20 2016-06-20 クラリアント・インターナシヨナル・リミテツド 油性物質、脂肪酸、アミノ酸界面活性剤、およびｎ−メチル−ｎ−アシルグルカミンを含有する組成物
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions

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DE4344991A1 (de) * 1993-12-30 1995-07-06 Huels Chemische Werke Ag Verfahren zur Umwandlung hexagonal flüssig-kristalliner wäßriger Tensidphasen
USH1513H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Oleoyl sarcosinate with polyhydroxy fatty acid amides in cleaning products

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WO1992006150A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions detergentes contenant un amide de l'acide gras de polyhydroxy et un sulfonate d'alkyle benzene
WO1992006152A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Amides de l'acide gras de polyhydroxy dans des compositions detergentes contenant un agent antisalissures
WO1992006171A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions detergentes liquides
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WO1992006162A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Detergent contenant des tensioactifs de sulfate d'alkyle et d'amide de l'acide gras de polyhydroxy

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US5174927A (en) * 1990-09-28 1992-12-29 The Procter & Gamble Company Process for preparing brightener-containing liquid detergent compositions with polyhydroxy fatty acid amines
US5188769A (en) * 1992-03-26 1993-02-23 The Procter & Gamble Company Process for reducing the levels of fatty acid contaminants in polyhydroxy fatty acid amide surfactants
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides

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WO1992006150A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions detergentes contenant un amide de l'acide gras de polyhydroxy et un sulfonate d'alkyle benzene
WO1992006152A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Amides de l'acide gras de polyhydroxy dans des compositions detergentes contenant un agent antisalissures
WO1992006171A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Compositions detergentes liquides
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WO1992006162A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Detergent contenant des tensioactifs de sulfate d'alkyle et d'amide de l'acide gras de polyhydroxy

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0675194A1 (fr) * 1994-03-28 1995-10-04 The Procter & Gamble Company Additifs pour détergents dans des liquides structurés
WO1995026392A1 (fr) * 1994-03-28 1995-10-05 The Procter & Gamble Company Additifs pour detergent incorpores dans des liquides structures
WO1996002620A1 (fr) * 1994-07-19 1996-02-01 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents a pouvoir ameliore de lavage
EP0738778A1 (fr) * 1995-04-19 1996-10-23 The Procter & Gamble Company Compositions détergentes non-aqueuses liquides contenant des particules
WO2009060312A3 (fr) * 2007-08-17 2009-11-05 Rhodia Asia Pacific Pte, Limited Compositions de savon structuré
US9090861B2 (en) 2007-08-17 2015-07-28 Rhodia Asia Pacific Ltd. Structured soap compositions
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
JP2016517852A (ja) * 2013-04-20 2016-06-20 クラリアント・インターナシヨナル・リミテツド 油性物質、脂肪酸、アミノ酸界面活性剤、およびｎ−メチル−ｎ−アシルグルカミンを含有する組成物
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints

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IE930417A1 (en) 1993-12-15
AU4233993A (en) 1993-12-30
CA2136947A1 (fr) 1993-12-09
JPH07507341A (ja) 1995-08-10
CN1079507A (zh) 1993-12-15
WO1993024602A1 (fr) 1993-12-09
TR26929A (tr) 1994-08-24

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