US3668136A - Compatible anionic-catonic surfactant compositions - Google Patents

Compatible anionic-catonic surfactant compositions Download PDF

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US3668136A
US3668136A US839698A US3668136DA US3668136A US 3668136 A US3668136 A US 3668136A US 839698 A US839698 A US 839698A US 3668136D A US3668136D A US 3668136DA US 3668136 A US3668136 A US 3668136A
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fatty acid
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sulfonates
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Graham Barker
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Witco Corp
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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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/047—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on cationic surface-active compounds and soap
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active 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
    • 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
    • C11D1/62—Quaternary ammonium compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/05—Organic amine, amide, or n-base containing

Definitions

  • This invention relates to novel compositions of matter com prising mixtures of cationic surfactants of specific structure and anionic surfactants generally, the compositions having unique surface active properties in aqueous solution. More specifically this invention relates to mutually compatible mixtures of anionic surfactants and cationic detergents comprising quaternary ammonium compounds having a polyoxyalkylene group linked to the nitrogen.
  • anionic surfactants or detergents which are disclosed in said patent as possessing the foregoing compatibility with said cationic surfactants are mono-alkali metal salts of polybasic carboxylic acid mono-esters of the terminal alkylol group of a poly-oxyalkylated organic compound containing a hydrophobic hydrocarbon radical on the opposite end of the poly-oxyalkylene chain which contains from about two to 20 oxyalkylene units having from two to three carbon atoms per unit, the said hydrophobic hydrocarbon radical containing from eight to about 21 carbon atoms.
  • cationic surfactants having a quaternary ammonium radical and a hydrophobic hydrocarbon group as, for instance, cetyldimethylethylammonium chloride, or other cationic surfactants disclosed in the aforesaid U.S. Pat. No.
  • 3,345,300 are admixed with numerous other anionic surfactants or detergents, such as, and particularly, those of the sulfate, sulfonate and phosphate ester types, such as sodium lauryl sulfate, sodium salts of sulfated higher fatty acid monoglycerides, dodecylbenzene sodium sulfonate, and sodium salts of phosphate esters of ethoxylated long chain alcohols and sodium salts of phosphate esters of ethoxylated long chain alkylphenols, incompatibility occurs in aqueous media and surfactant activity is effectively destroyed, precipitation usually occurring.
  • column 10 last two lines, and column 11, lines 18 of said U.S. Pat. No. 3,345,300. See, also, U.S. Pat. No. 2,213,477.
  • compositions are characterized by excellent compatibility in aqueous media and improved surface active characteristics, particularly with regard to foam boosting and stabilization, viscosity and solubilization in high-solid compositions.
  • novel cationic surfactant-anionic surfactant compositions are especially suitable for use in cosmetic detergent formulations such as shampoos, body detergents, facial cleansers, bubble baths and the like because of the foam boosting and stabilization effect and the solubilization of germicidal ingredients such as hexachlorophene without the need for addition of inactive ingredients such as ethylene glycols or propylene glycols which are generally used for such purposes.
  • the particular types of cationic surfactants which are utilized offer a distinct ad vantage over the commonly employed fatty amide and alkanolamide foam boosters and stabilizers which tend to build up viscosity, whereas said cationic surfactants function, in
  • viscosity reducing agents thus offering, in the compositions of this invention, the highly desirable feature of simultaneously building foam and reducing viscosity.
  • cationic quaternary ammonium compounds disclosed in the aforesaid U.S. Pats. Nos. 3,123,640; 3,123,641; 3,141,905 and 3,155,591, are represented by the formula wherein R is an alkyl radical containing from one to three carbon atoms, and more particularly from one to two carbon atoms, R, is an alkyl radical containing from one to three carbon atoms, and compounds wherein R and R, are joined together to form with the N atom a member of the group consisting of piperidine, methyl piperidine and pyrrolidine;
  • R is an alkyl radical containing from one to four carbon atoms, n is a number up to and including 60, the total number of carbon atoms in R being at least 18; R is a member selected from the group consisting of 1) alkyl and alkenyl radicals containing not more than four carbon atoms, and (2) benzene; methyl benzenes; ethyl benzenes;
  • R may comprise other radicals over and above those identified above, as, for instance, isopropyl benzene, naphthalene, methyl naphthalenes and isopropyl naphthalene.
  • R may be a radical of a cyclic amine containing not more than six carbon atoms
  • R is a polyoxyalkylene radical containing at least 18 carbon atoms and derived from an a-epoxide containing at least three carbon atoms, especially propyleneoxide.
  • R is derived from propyleneoxide
  • R is derived from a-epoxides containing more than three carbon atoms, a lesser number of such oxyalkylene groups can be present, subject to the limitation of R, containing at least 1 8 atoms.
  • R is advantageously a lower alkyl or alkenyl radical containing from one to four carbon atoms; or a lower aliphatic-aryl radical containing seven to nine carbon atoms, notably an alkaryl radical; and A is an anion, it being important that the R radial, where it is alkyl, contain not more than three carbon atoms and especially that it contain from one to two carbon atoms and, hence, that it be methyl or ethyl; that, except where is derived from a cyclic amine, as hereafter pointed out, the R, radical does not contain over three carbon atoms, and, in any event, that the maximum number of carbon atoms in R and R, does not exceed a total of four or five; and that, while R may contain a minimum of six of the aforesaid oxyalkylene, particularly oxypropylene groups, and may contain 40, 50 or 60 or even 100 or more of said groups, the minimum number of said groups be eight, with the preferred range being 8 to 25
  • R is where R is an alkyl radical containing from one to four carbon atoms, n and n are numbers the sum of which preferably does not exceed 60, the total number of carbon atoms in R, and R being at least 18; R is a hydrocarbon radical selected from the group consisting of alkyl and alkenyl radicals containing not more than four carbon atoms, or a lower aliphaticaromatic hydrocarbon radical containing from seven to nine carbon atoms; and A is an anion.
  • R is an alkyl radical containing from one to three, and especially from one to two carbon atoms
  • R is an alkyl radical containing from one to three carbon atoms
  • alkylene contains not more than three carbon atoms
  • R. is an alkyl radical containing from one to four carbon atoms, n is a number up to and preferably not exceeding 60, the total number of carbon atoms in R being at least 18;
  • R is a hydrocarbon radical selected from the group consisting of alkyl and alkenyl radicals containing not more than four carbon atoms, or a lower aliphatic-aromatic hydrocarbon radical containing from seven to nine carbon atoms; and
  • A is an anion.
  • R,-O-alkyleneN where alkylene contains not more than 3 carbon atoms, RO is in which R4 is an alkyl radical containing from one to four carbon atoms, n, n and nare numbers the sum of which preferably does not exceed 60, the total number of carbon atoms in R, R, and R being at least 18; R is a hydrocarbon radical selected from the group consisting of alkyl and alkenyl radicals containing not more than four carbon atoms, or a lower aliphaticaromatic hydrocarbon radical containing from seven to nine carbon atoms; and A is an anion.
  • quaternary ammonium type compounds having utility in the present invention fall into the category of or correspond to reaction products of quaternizing esters having a hydrocarbon alkyl or alkenyl radical containing not more than four carbon atoms, or a benzyl radical or a dimethylbenzyl radical or a lower alkylsubstituted or' chloror nitro-substituted benzyl radical, and an anion, with adducts of (a) aliphatic amines or cyclic amines containing a reactive hydrogen and a total of not more than six carbon atoms and in which no single aliphatic radical contains more than three carbon atoms, with (b) an a-epoxide containing at least three and advantageously from three to eight carbon atoms, the molal ratio of (a) to (b) being 1 of (a) to at least 6 of (b) when said a-epoxide contains three carbon atoms and ranging down to at least 2.5 of (
  • R is an alkyl radical containing from one to three carbon atoms
  • R is an alkyl radical containing from one to three carbon atoms or is the same as R
  • R is a polyoxyalkylene radical containing at least 18 carbon atoms and derived from an a-epoxide containing from three to eight carbon atoms
  • R is a hydroxy-alkyl radical containing from two to four carbon atoms
  • A is hydroxyl or other anion.
  • Such compounds are readily :produced by reacting the adducts, such as those described in Examples a to v of US. Pat. No.
  • quaternary ammonium compounds which are particularly useful are reaction products of quaternizing esters in the form of alkyl and alkenyl halides, sulfates and sulfonates containing from one to four carbon atoms, exemplified by methyl chloride, ethyl chloride, methyl chloracetate, and one and two carbon atom alkyl sulfates; or aromatic quaternizing esters in the form of halides, sulfates and sulfonates advantageously containing from seven to nine carbon atoms, exemplified by benzyl chlorides, dimethylbenzyl chloride, and phenylethyl chloride, with adducts of (0) alkyl amines having
  • the oxyalkylene groups substituted on the quaternary ammonium type compounds be derived from an a-epoxide containing at least three carbon atoms.
  • the most important embodiment of the a-epoxide whose use is contemplated herein in the production of the desired quaternary ammonium type compounds is propyleneoxide
  • the a epoxides containing four, five, six or more carbon atoms can be used but, for general reasons of lack of economy or commercial availability, are not preferred.
  • a-epoxides Typical of such latter a-epoxides are butyleneoxides such as l,2-butyleneoxide, pentylene epoxides, hexylene epoxides, heptylene epoxides, octylene epoxides, dodecylene epoxides, and C C, olefin oxides or epoxides, and, as well, styrene epoxide. It will be seen that most of those of the a-epoxides in which the vicinal carbons are terminal can conveniently by represented by the formula where R is an alkyl radical.
  • R is CH and in the representation of the group of propyleneoxide, butyleneoxides, pentyleneoxide and hexyleneoxide R contains from one to four carbon atoms. In the higher molecular weight alkylene oxides, R may contain as high as 16 carbon atoms.
  • ethylene oxide cannot be employed as the sole alkylene oxide in preparing the quaternary ammonium cationic surfactants useful in preparing the novel anionic-cationic surfactant compositions of the present invention
  • minor proportions thereof, not to exceed about 20 percent by weight of the propylene oxide, or other a-epoxide employed, can be utilized as hereafter described.
  • Mixtures of two or more of the a-epoxides containing at least three carbon atoms can, of course, be used as such, as well as in conjunction with ethylene oxide, subject to the limitation that the ethylene oxide must not exceed the aforesaid 20 percent of the weight of said a-epoxides.
  • the radical A can be any negative or salt-forming radical as, for instance, halogen such as chlorine, bromine and iodine; hydroxy; sulfate, alkyl-sulfuric acid such as methyl sulfuric acid or ethyl sulfuric acid (methosulfate of ethosulfate); nitrate; phosphate; acetate; formate; carbonate; lower alkyl (one to four carbon atoms) sulfonic acids; and the like.
  • halogen such as chlorine, bromine and iodine
  • hydroxy sulfate, alkyl-sulfuric acid such as methyl sulfuric acid or ethyl sulfuric acid (methosulfate of ethosulfate); nitrate; phosphate; acetate; formate; carbonate; lower alkyl (one to four carbon atoms) sulfonic acids; and the like.
  • quaternary ammonium type compounds in which the anion is chlorine, bromine,
  • the anionic surfactants which are compatible with the aforesaid quaternary ammonium compounds described herein, which mixtures form the novel compositions of the present invention, comprise a broad spectrum of compounds, as is well known to those skilled in the art.
  • Members of this classification comprise the water-soluble salts such as the alkali metal and amine soaps of straight and branched chain fatty acids, said fatty acids being both naturally occurring, such as from coconut oil or from tall oil, and synthetically produced such as by paraffin oxidation; the water soluble salts of organic sulfonic acids, alkyl sulfuric acids and sulfuric acid esters of polyhydric alcohols incompletely esterified with a fatty acid of high molecular weight, sulfated and sulfonated higher fatty acid amides and alkanolamides which include the sulfated fatty oil, sulfated fatty acids, sulfated straight chain and branched chain C -C alcohols, sulfated alkyl
  • alkyl sulfates prepared by reacting a fatty alcohol with sulfuric acid or chlorosulfonic acid, said fatty alcohol having from about eight to 18 carbon atoms, of particular utility in preparing the compositions of the present invention being the alkali metal, alkaline earth metal, ammonium, lower amine and a1- kanolamine alkyl sulfates wherein the alkyl group contains from eight to 18 carbon atoms.
  • alkanesulfonates such as the di-alkyl sulfo-succinates, amide linked sulfonates and various derivatives thereof.
  • alkylaryl sulfonates both straight and branched chain, sodium dodecylbenzene sulfonate being the common commercial product.
  • alkylaryl sulfonates usually contain from about six to 26 carbon atoms in the alkyl chain.
  • alkylaryl sulfonates may also contain intermediate linkages such as amide and hydrazide linkages, as exemplified by the sulfonated a-alkylbenzimidazoles, and ester and ether linkages.
  • intermediate linkages such as amide and hydrazide linkages, as exemplified by the sulfonated a-alkylbenzimidazoles, and ester and ether linkages.
  • suitable anionic surfactants are the esters of the oxy acids of phosphorous with aliphatic alcohols having from about six to 18 carbon atoms and alkyl phenols wherein the alkyl chain contains from eight to 18 carbon atoms.
  • anionic detergents wherein the anionic surfactant solubilizing group is a member selected from the group consisting of SO H, SO H, COOH and the water-soluble salts thereof especially the alkali metal, alkaline earth metal, ammonium and lower amine and alkanolamine salts.
  • anionic surfactants are disclosed in numerous patents among which may be mentioned, by way of illustration, U.S. Pat. Nos. 2,383,737; 2,486,921; 2,920,045; and 3,004,056.
  • the aforesaid quaternary ammonium surfactant may be combined with the aforesaid anionic surfactants over a wide range of proportions, since the compatibility is not limited by any critical weight proportions, and there will be no significant diminution of surface active properties, no matter what the ratio of the said surfactants may be to each other.
  • the aforesaid quaternary ammonium surfactant there is employed from about 20 to 40 percent, better still about 25 to 30 percent, of said quaternary ammonium surfactant, based on the weight of combined cationic and anionic surfactants in the compositions.
  • EXAMPLE 1 The following tabulated data represent the results of the Shake Foam Test (50 mls total liquid in 250 ml cylinder, 20 inversions).
  • the anionic surfactant employed was sodium lauryl sulfate; the cationic surfactant was a quaternary ammonium compound of the formula Cg: Cal-I /1 CH3 R Cl but a cationic surfactant similar to that in Example 1 was employed except the polyoxypropylene radical contained about 30 oxypropylene groups.
  • EXAMPLE 3 The shake foa'm test was repeated with the cationic surfac- 40 tant of Example 1 and the triethanolamine salt of dodecylbenzene sulfonic acid as the anionic surfactant.
  • compositions made in accordance with the present invention are as follows, the pro portions stated being in weight percent.
  • EXAMPLE 6 Phosphate ester of [0 mol ethylene oxide adduct of nonyl phenol (sodium salt) 25 mol propylene oxide adduct of dimethylamine quaternized with ethyl chloride
  • EXAMPLE 7 Phosphate ester of 12 mol ethylene oxide adduct of dodecyl alcohol (triethanolamine salt) 16 mol propylene oxide adduct of methylethylamine quaternized with benzyl chloride
  • EXAMPLE 8 Why acid monoester of sulfuric acid monoester of glycerol (triethanolamine salt) 18 mol propylene oxide adduct of dimethylethanolamine quatemized with methyl chloracetate
  • EXAMPLE 9 Sodium lauryl sulfate 70% 12 mol butylene oxide adduct of dimethylamine quaternized with dimethyl sulfate wherein R is alkyl containing from one to three carbon atoms, R, is
  • composition according to claim 1 wherein the anionic surfactant is selected from the group consisting of alkyl sulfates, alkylaryl sulfonates and fatty carboxylic acid soaps 3.
  • the anionic surfactant is an alkali metal alkyl sulfate wherein the alkyl group contains from eight to 18 carbon atoms.
  • composition according to claim 2 wherein the anionic surfactant is an alkali metal alkyl benzene sulfonate wherein the alkyl group contains from eight to 18 carbon atoms.
  • composition according to claim 1 in which the R radical of said cationic surfactant compound contains a polyoxyethylene radical in which the ethylene oxide constitutes not more than 20 percent by weight of said R radical.
  • R is alkyl containing from one to four carbon atoms, n and n are numbers the sum of which does not exceed 60, the total number of carbon atoms in R, and R being at least 18;
  • R is a member selected from the group consisting of l alkyl and alkenyl containing not more than four carbon atoms, and (2)benzene; methyl benzenes', ethyl benzenes;
  • A is an innocuous anion.
  • a composition consisting essentially of a water-soluble I anionic surfactant being a member selected from the group consisting of fatty acid soaps, alkyl sulfates sulfates of polyhydric alcohols partially esterified with a fatty acid, sulfated and sulfonated fatty acid amides and alkanolamides, alkane-sulfonates, ester-, etherand amide-linked sulfonates, alkylaryl sulfonates and phosphates of aliphatic alcohols and alkyl phenols and from about 20 to 40 percent by weight of a cationic surfactant, based on the weight of combined cationic and anionic surfactants, corresponding to the formula where R is alkyl containing from one to three carbon atoms, alkylene contains not more than three carbon atoms, R,-0 is and their methyl and ethyl nuclearly substituted derivatives; and the mono-halo and mono-nitro nuclearly substitute
  • a composition consisting essentially of a water-soluble anionic surfactant being a member selected from the group consisting of fatty acid soaps, alkyl sulfates, sulfates of polyhydric alcohols partially esterified with a fatty acid, sulfated and sulfonated fatty acid amides and alkanolamides, alkane-sulfonates, ester-, etherand amide-linked sulfonates, alkylaryl sulfonates and phosphates of aliphatic alcohols and alkyl phenols and from about 20 to 40 percent by weight of a cationic surfactant, based on theweight of combined cationic and anionic surfactants, corresponding to the formula where alkylene contains not more than three carbon atoms,
  • R is alkyl containing from one to four carbon atoms, n, n and n are numbers the sum of which does not exceed 60, the total number of carbon atoms in R, R and R being at least 18;
  • R is a member selected from the group consisting of 1) alkyl and alkenyl containing not more than four carbon atoms, and (2)benzene; methyl benzenes; ethyl benzenes;
  • A is an innocuous anion.
  • atoms is R; being at least 18, v is a number at least 1 with the proviso that the weight ratio of (C Ht0-), to R is not greater than one to four,
  • X is a member selected from the group consisting of (l alkyl and alkenyl containing from one to four carbon atoms, and (2) benzene; lower alkyl benzenes in which the lower alkyl contain from one to four carbon and their methyl and ethyl nuclearly substituted derivatives;
  • R is alkyl containing from one to four carbon atoms
  • n is a number up to and including 60, the total number of carbon atoms in R being at least 18
  • v is a number at least 1 with the proviso that the weight ratio of (C H -O-),. to R is not greater than one to four
  • X is a member selected from the group consisting of l alkyl and alkenyl containing from one to four carbon atoms, and benzene; lower alkyl benzenes in which the lower alkyls contain from one to four carbon atoms,
  • a composition consisting essentially of a water-soluble anionic surfactant being a member selected from the group consisting of fatty acid soaps, alkyl sulfates, sulfates of polyhydric alcohols partially esterified with a fatty acid, sulfated and sulfonated fatty acid amides and alkanolamides, alkane-sulfonates, ester-, etherand amide-linked sulfonates, alkylaryl sulfonates and phosphates of aliphatic alcohols and alkyl phenols and from about 20 to 40 percent by weight of a cationic surfactant, based on the weight of combined cationic and anionic surfactants, corresponding to the formula where R is an alkyl containing from one to three carbon atoms R is greater than one to four, X is a member selected from the group consisting of 1) alkyl and alkenyl containing from one to four carbon atoms, and (2) benzene;

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2397476A1 (fr) * 1977-07-11 1979-02-09 Richardson Co Bain acide destine a la production d'un depot electrolytique brillant de zinc et ses applications
US4247538A (en) * 1978-09-05 1981-01-27 Witco Chemical Corporation Conditioning shampoo
US4303543A (en) * 1979-02-27 1981-12-01 The Procter & Gamble Company Method for cleansing and conditioning the skin
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
JPH05194152A (ja) * 1991-09-12 1993-08-03 Unilever Nv ヘアコンディショニング組成物
US5298193A (en) * 1989-04-06 1994-03-29 Hoechst Aktiengesellschaft Low-foaming and low-temperature-stable liquid surfactant compositions composed of water and nonionic, anionic and cationic surfactants and the use thereof
WO1997043371A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
WO1997044420A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
WO1997044425A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
WO2000063331A1 (en) * 1999-04-20 2000-10-26 Ecolab Inc. Composition and method for road-film removal
US6339054B1 (en) 1999-04-20 2002-01-15 Ecolab, Inc. Composition and method for road-film removal
US6551974B1 (en) 1999-04-20 2003-04-22 Ecolab Inc. Polish compositions for gloss enhancement, and method
US8557756B2 (en) 2010-06-29 2013-10-15 Dow Global Technologies Llc Compatible mixtures of anionic and cationic surfactants
CN116023308A (zh) * 2021-10-26 2023-04-28 中国石油化工股份有限公司 一种稠油降粘剂及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5352799A (en) * 1976-10-19 1978-05-13 Kao Corp Fabric softening agent composition
JPS5527134A (en) * 1978-08-15 1980-02-27 Kao Corp Hair rinse composition

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2734830A (en) * 1950-01-13 1956-02-14
GB873214A (en) * 1958-08-20 1961-07-19 British Nylon Spinners Ltd Non-ionic detergent compositions
US3123640A (en) * 1964-03-03 Cation-active surface active aryldi-
US3123641A (en) * 1964-03-03 Cation-active surface active trilower-
US3141905A (en) * 1963-04-29 1964-07-21 Witco Chemical Corp Cation-active surface active quaternary ammonium compounds
US3155591A (en) * 1961-12-06 1964-11-03 Witco Chemical Corp Hair rinse compostions of polyoxypropylene quaternary ammonium compounds
US3325414A (en) * 1963-10-01 1967-06-13 Colgate Palmolive Co Heavy duty detergent composition containing a quaternary ammonium salt
US3345300A (en) * 1967-10-03 Ohj-ohi

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3123640A (en) * 1964-03-03 Cation-active surface active aryldi-
US3123641A (en) * 1964-03-03 Cation-active surface active trilower-
US3345300A (en) * 1967-10-03 Ohj-ohi
US2734830A (en) * 1950-01-13 1956-02-14
GB873214A (en) * 1958-08-20 1961-07-19 British Nylon Spinners Ltd Non-ionic detergent compositions
US3155591A (en) * 1961-12-06 1964-11-03 Witco Chemical Corp Hair rinse compostions of polyoxypropylene quaternary ammonium compounds
US3141905A (en) * 1963-04-29 1964-07-21 Witco Chemical Corp Cation-active surface active quaternary ammonium compounds
US3325414A (en) * 1963-10-01 1967-06-13 Colgate Palmolive Co Heavy duty detergent composition containing a quaternary ammonium salt

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2397476A1 (fr) * 1977-07-11 1979-02-09 Richardson Co Bain acide destine a la production d'un depot electrolytique brillant de zinc et ses applications
US4247538A (en) * 1978-09-05 1981-01-27 Witco Chemical Corporation Conditioning shampoo
US4303543A (en) * 1979-02-27 1981-12-01 The Procter & Gamble Company Method for cleansing and conditioning the skin
US4664848A (en) * 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US5298193A (en) * 1989-04-06 1994-03-29 Hoechst Aktiengesellschaft Low-foaming and low-temperature-stable liquid surfactant compositions composed of water and nonionic, anionic and cationic surfactants and the use thereof
JPH05194152A (ja) * 1991-09-12 1993-08-03 Unilever Nv ヘアコンディショニング組成物
WO1997043371A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
WO1997044420A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
WO1997044425A3 (en) * 1996-05-17 1997-12-24 Procter & Gamble Detergent composition
US6136769A (en) * 1996-05-17 2000-10-24 The Procter & Gamble Company Alkoxylated cationic detergency ingredients
US6350725B1 (en) 1999-04-20 2002-02-26 Ecolab, Inc. Composition and method for road-film removal
US7223722B2 (en) 1999-04-20 2007-05-29 Ecolab Inc. Polish compositions for gloss enhancement, and method
WO2000063331A1 (en) * 1999-04-20 2000-10-26 Ecolab Inc. Composition and method for road-film removal
US6551974B1 (en) 1999-04-20 2003-04-22 Ecolab Inc. Polish compositions for gloss enhancement, and method
US6602350B2 (en) 1999-04-20 2003-08-05 Ecolab Inc. Composition and method for road-film removal
US6864220B2 (en) 1999-04-20 2005-03-08 Ecolab Inc. Composition and method for road-film removal
US20050199272A1 (en) * 1999-04-20 2005-09-15 Ecolab Inc. Composition and method for road-film removal
US6339054B1 (en) 1999-04-20 2002-01-15 Ecolab, Inc. Composition and method for road-film removal
US7482315B2 (en) 1999-04-20 2009-01-27 Ecolab Inc. Composition and method for road-film removal
US20090188533A1 (en) * 1999-04-20 2009-07-30 Ecolab Inc. Composition and method for road-film removal
US7951245B2 (en) 1999-04-20 2011-05-31 Ecolab Usa Inc. Composition and method for road-film removal
US8557756B2 (en) 2010-06-29 2013-10-15 Dow Global Technologies Llc Compatible mixtures of anionic and cationic surfactants
CN116023308A (zh) * 2021-10-26 2023-04-28 中国石油化工股份有限公司 一种稠油降粘剂及其制备方法和应用
CN116023308B (zh) * 2021-10-26 2024-05-03 中国石油化工股份有限公司 一种稠油降粘剂及其制备方法和应用

Also Published As

Publication number Publication date
FR2054161A5 (enrdf_load_stackoverflow) 1971-04-16
GB1320566A (en) 1973-06-13
DE2025481A1 (de) 1971-01-14

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