US2875153A - Detergent compositions - Google Patents

Detergent compositions Download PDF

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US2875153A
US2875153A US504359A US50435955A US2875153A US 2875153 A US2875153 A US 2875153A US 504359 A US504359 A US 504359A US 50435955 A US50435955 A US 50435955A US 2875153 A US2875153 A US 2875153A
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soap
detergent
gel
water
ionic
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US504359A
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Dalton Philip Benjamin
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Colgate Palmolive Co
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Colgate Palmolive Co
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/045Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on non-ionic surface-active compounds and soap
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/74Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • This invention relates to novel detergent compositions in the form of a gel comprising soap, liquid non-ionic polyalkylene oxide detergent and water, as hereinafter described.
  • soap and synthetic detergents may be compounded together to obtain certain desirable characteristics, such as improved lime soap dispersion.
  • the proposed synthetic detergents have been usually of the anionic sulfate or sulfonate type. It has been proposed that soap may be used in admixture with certain non-ionic polyalkylene oxide detergents, particularly to produce non-foaming compositions.
  • the addition of certain inorganic materials such asborax as an essential ingredient with these mixed detergents has been suggested for the manufacture of solid compositions.
  • a detergent composition in the form of a gel which exhibits many desirable characteristics and consists essentially of water-soluble soap, water-soluble liquid non-ionic polyalkylene oxide detergent and water in certain proportions necessary to the formation of the gel state. More particularly, the gel composition may be formed by suitable proportioning of the ingredients so as to-form a gel consisting essentially of about 40 to about 60% by weight of a mixture of said soap and non-ionic detergent in a ratiofrom about 4:1 to about 1:12 by weight.
  • Such novel compositions are characterized by their gelled appearance and structure, their relatively dry physical form even though an appreciable amount of liquid non-ionic detergent is present therein, their ready solubility in water, efficient cleansing and lime soap dispersing properties in soft and hard water andia high level of foaming power.
  • the novel gel composition has as an essential ingredient water-soluble soap, particularly the water-soluble higher fatty acid soap.
  • water-soluble soap particularly the water-soluble higher fatty acid soap.
  • These soaps may beproduced' by the saponification of fatty materials or the like suitable for use in soap-making.
  • suitable fatty materials are the fats, oils,'and waxes of animal, vegetable and marine origin and the fatty acids derivedtherefrom or of synthetic origin. More specifically, the higher fatty acids may be derived from tallow, cottonseed oil, coconut oil, palm oil, palm kernel oil, grease, fish oils, and suitable mixtures thereof, etc.
  • These water-soluble soaps are in the form of their alkali metal or "nitrogen-containing salts.
  • the alkali metal soaps it"is'preferred to use the sodium and potassium soaps.
  • suitable nitrogen-containing soaps argihe ammonium soaps and alkylolamine soaps; e. g., mono-, di-, and triethanolamine soaps.
  • suitable soaps are the sodium and potassium soaps of .lauric.acid, myristic acid; palmitic acid, stearic acid, oleicacid; coconut fattylacids,
  • soap used in the preparation of these compositions may be of any titer.
  • soap which is readily soluble in water such as soap of relatively low titer, as for example, up to about 40 C. and preferably from about 8 to 30 C. titer.
  • the essential synthetic detergent component is a watersoluble non-ionic polyalkylene oxide detergent which is liquid at normal room temperature of the order of about 20 C.
  • these detergents are the products produced by the introduction of a controlled number of alkylene oxide groups into an organic hydrophobic compound or group, usually of an aliphatic or aromatic structure.
  • the degree or proportion of hydrophilic groups will vary with the specific hydrophobic group, but in general will be sufiicient to confer the desired watersolubility and detersive properties.
  • These detergents are known in the art and the determination of a specific hydrophiliczhydrophobic relationship for each type is not the essential novelty of the present invention.
  • the hydrophobic organic group contains at least about 8 carbons, and preferably up to 30 carbons, condensed with at least about 5 and usually up to about 50 alkylene oxide groups. It is preferred to use the polyoxyethylene condensates derived from ethylene oxide although other lower alkylene oxides, such as propylene oxide, butylene oxide and the like have generally similar properties and may be substituted therefor.
  • the polyalkylene oxide condensates of alkyl phenol such as the polyoxyethylene ether of alkyl phenols having an alkyl group of at least about 'six, and usually about 8 to 12 carbons, and an ethylene oxide ratio (number of moles per phenol) of about 7.5, 8.5, 11.5 and 20, though the number of ethylene oxide groups will be usually from about 8 to 18.
  • alkyl substituent on the aromatic nucleus may be diisobutylene, diarnyl, polymerized propylene, dimerized C -C olefin, and the like.
  • detergents are the polyoxyalkylene esters of organic acids, such as the higher fatty acids or tall oil acids.
  • the polyglycol esters will contain usually from about 12 to about 30 moles of ethylene oxide and about 8 to 22 carbons in the acyl group.
  • a suitable example is refined tall oil condensed with about 16-20 ethylene oxide groups.
  • the gelled detergent composition may be formed by suitable proportioning of these detersive ingredients in the proper ratio with controlled amounts of water to form thegel.
  • the mixture solidifies to a heavy gel, the consistency of which depends upon the precise ratio of the several ingredients.
  • This gel is substantially uniform in nature and of relatively dry form, varying in physical state from a solid to a the mixture and maybe conducted over a wide range of suitable temperaturessuch as from about room temperature to about 212 F.
  • the gels exhibit a high level of cleansing and lime soap dispersing properties in soft and hard water, and have many useful fields of application.
  • the gels may. be used as shampoos and as general washing and cleansing compositions. They may be dried in" any suitable manner to reduce the-water content to a pre-i determined level or to the equilibrium point to obtain substantially anhydrous material which may be subjected to mechanical Working to produce a particular type of product. For example, such material may be milled to obtain flakes or ribbons, and, if desired, .plodded in the usual manner using conventional soap-making machinery to form bars or cakes which have a characteristic translucent appearance.
  • adjuvant materials may be employed in the gel compositions of the present invention.
  • Such materials may include perfume, coloring material, germicide and the like.
  • EXAMPLE II 131 parts of the 36% potassium soap solution used in Example I are admixed with 44 parts of the Igepal CA with stirring, resulting in the obtention of a heavy White gel solid having approximately non-ionic, 27% anhydrous soap and 48% water. This gel exhibits good foaming and detersive properties.
  • EXAMPLE III parts of roll-dried potassium soaps of coconut fatty acid and red oil in a 3:1 ratio are admixed with 53 parts water and 16.6 parts Igepal CA with stirring, resulting in the formation of a solid gel. This gel exhibits satisfactory washing power.
  • EXAMPLE IV 800 parts of white flaked soap comprising a mixture of sodium salts of fatty acids derived from 75% coconut oil and 25% tallow fatty acids are admixed with 720 parts of water. This aqueous soap mixture is heated to 150 F. and 200 parts of the Igepal CA are added thereto. The resulting mixture is heated at 150 F. with stirring for 15 minutes and then it was allowed to cool to a gel. The gelled mixture exhibits satisfactory washing properties. A portion of the gel is dried to equilibrium moisture, milled to form shiny transparent-like flakes which are plodded to produce a detergent bar having a translucent appearance.
  • EXAMPLE V parts of the 36% potassium soap solution of Example I are mixed with 10 parts of a condensate of tall oil with 16-20 ethylene oxide groups, resulting in the formation'of a gel. This gel had about 10% non-ionic detergent, 32% soap and 58% water, and exhibits satisfactory detersive and foaming power also.
  • the admixture of parts of the soap solution to 5 parts of the non-ionic detergent results in an essentially liquid system having 5% non-ionic, 34% soap and 61% Water.
  • the admixture of 50 parts non-ionic to 50 parts of the soap solution results in a completely liquid system also having 50% non-ionic, 18% soap and water as the balance.
  • a detergent composition in the form of a gel havin a relatively dry form and consisting essentially of watersoluhle higher fatty acid soap, water-soluble non-ionic liquid polyoxyethylene esters of tall oil detergent having about 12 to about 30 moles of ethylene oxide and water, said soap being derived from a mixture of about 75% coconut oil fatty acids and 25 fatty acid selected from the group consisting of-Loleic acid and tallow fatty acids, the amount of said soap and non-ionic detergent being from about 40 to about 60% by weight of said gel and the ratio from about 4:1 to about 1:1.2 by weight.
  • -A detergent composition in the form of a gel having a. relatively dry form and consisting essentially of watersoluble higher fatty acid soap, water and water-soluble non-ionic normally liquid polyalkylene oxide detergent selected from the group consisting of polyoxyalkylene condensates of higher alkyl phenol and polyoxyalkylene esters of higher fatty acids, said soap being derived from a mixture of about 75% coconut oil fatty acids and 25% fatty acid selected from the group consisting of oleic acid and tallow fatty acids, and said non-ionic detergent containing from 5 to 50 moles of alkylene oxide of 2 to 4 carbon atoms each, the amount of said soap and nonionic detergent being from about 40 to about 60% by weight and in a ratio from about 4:1 to 1:1.2 by 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)
  • Detergent Compositions (AREA)

Description

United States Patent" DETERGENT COMPOSITIONS Philip Benjamin Dalton, Franklin Square, N. Y., assignor to Colgate-Palmolive Company, Jersey City, N. J., a corporation of Delaware No Drawing. Application April 27, 1955 Serial No. 504,359
5 Claims. (Cl. 252132) This invention relates to novel detergent compositions in the form of a gel comprising soap, liquid non-ionic polyalkylene oxide detergent and water, as hereinafter described.
It has been suggested that soap and synthetic detergents may be compounded together to obtain certain desirable characteristics, such as improved lime soap dispersion. The proposed synthetic detergents have been usually of the anionic sulfate or sulfonate type. It has been proposed that soap may be used in admixture with certain non-ionic polyalkylene oxide detergents, particularly to produce non-foaming compositions. The addition of certain inorganic materials such asborax as an essential ingredient with these mixed detergents has been suggested for the manufacture of solid compositions.
The physical state of a detergent composition is of fundamental consideration in the specific application, economics, consumer appeal and efficiency of the product. In general, mixtures of soap and synthetic detergents broadly have been proposed for use in the form of laundry or toilet bars, flakes, and as liquid shampoos.. I
It has now been discovered-that there may be prepared a detergent composition in the form of a gel which exhibits many desirable characteristics and consists essentially of water-soluble soap, water-soluble liquid non-ionic polyalkylene oxide detergent and water in certain proportions necessary to the formation of the gel state. More particularly, the gel composition may be formed by suitable proportioning of the ingredients so as to-form a gel consisting essentially of about 40 to about 60% by weight of a mixture of said soap and non-ionic detergent in a ratiofrom about 4:1 to about 1:12 by weight. Such novel compositions are characterized by their gelled appearance and structure, their relatively dry physical form even though an appreciable amount of liquid non-ionic detergent is present therein, their ready solubility in water, efficient cleansing and lime soap dispersing properties in soft and hard water andia high level of foaming power.
The novel gel composition has as an essential ingredient water-soluble soap, particularly the water-soluble higher fatty acid soap. These soaps may beproduced' by the saponification of fatty materials or the like suitable for use in soap-making. Among suitable fatty materials are the fats, oils,'and waxes of animal, vegetable and marine origin and the fatty acids derivedtherefrom or of synthetic origin. More specifically, the higher fatty acids may be derived from tallow, cottonseed oil, coconut oil, palm oil, palm kernel oil, grease, fish oils, and suitable mixtures thereof, etc. These water-soluble soaps are in the form of their alkali metal or "nitrogen-containing salts. Among the alkali metal soaps it"is'preferred to use the sodium and potassium soaps. Examples of'suitable nitrogen-containing soaps argihe ammonium soaps and alkylolamine soaps; e. g., mono-, di-, and triethanolamine soaps. Further examples of suitable soapsare the sodium and potassium soaps of .lauric.acid, myristic acid; palmitic acid, stearic acid, oleicacid; coconut fattylacids,
2,875,153 Patented Feb. 24,
tallow fatty acids, naphthenic and rosin acids, and the like The soap used in the preparation of these compositions may be of any titer. For optimum effects, it is desired to use soap which is readily soluble in water, such as soap of relatively low titer, as for example, up to about 40 C. and preferably from about 8 to 30 C. titer.
The essential synthetic detergent component is a watersoluble non-ionic polyalkylene oxide detergent which is liquid at normal room temperature of the order of about 20 C. In general, these detergents are the products produced by the introduction of a controlled number of alkylene oxide groups into an organic hydrophobic compound or group, usually of an aliphatic or aromatic structure. The degree or proportion of hydrophilic groups will vary with the specific hydrophobic group, but in general will be sufiicient to confer the desired watersolubility and detersive properties. These detergents are known in the art and the determination of a specific hydrophiliczhydrophobic relationship for each type is not the essential novelty of the present invention. In general, the hydrophobic organic group contains at least about 8 carbons, and preferably up to 30 carbons, condensed with at least about 5 and usually up to about 50 alkylene oxide groups. It is preferred to use the polyoxyethylene condensates derived from ethylene oxide although other lower alkylene oxides, such as propylene oxide, butylene oxide and the like have generally similar properties and may be substituted therefor.
It is preferred to use the polyalkylene oxide condensates of alkyl phenol, such as the polyoxyethylene ether of alkyl phenols having an alkyl group of at least about 'six, and usually about 8 to 12 carbons, and an ethylene oxide ratio (number of moles per phenol) of about 7.5, 8.5, 11.5 and 20, though the number of ethylene oxide groups will be usually from about 8 to 18. The alkyl substituent on the aromatic nucleus may be diisobutylene, diarnyl, polymerized propylene, dimerized C -C olefin, and the like.
Further suitable detergents are the polyoxyalkylene esters of organic acids, such as the higher fatty acids or tall oil acids. The polyglycol esters will contain usually from about 12 to about 30 moles of ethylene oxide and about 8 to 22 carbons in the acyl group. A suitable example is refined tall oil condensed with about 16-20 ethylene oxide groups.
The gelled detergent composition may be formed by suitable proportioning of these detersive ingredients in the proper ratio with controlled amounts of water to form thegel. Upon admixing the ingredients with stirring in order to form a substantially homogeneous mixture, the mixture solidifies to a heavy gel, the consistency of which depends upon the precise ratio of the several ingredients. This gel is substantially uniform in nature and of relatively dry form, varying in physical state from a solid to a the mixture and maybe conducted over a wide range of suitable temperaturessuch as from about room temperature to about 212 F.
These gel compositions exhibit a high level of cleansing and lime soap dispersing properties in soft and hard water, and have many useful fields of application. The gels may. be used as shampoos and as general washing and cleansing compositions. They may be dried in" any suitable manner to reduce the-water content to a pre-i determined level or to the equilibrium point to obtain substantially anhydrous material which may be subjected to mechanical Working to produce a particular type of product. For example, such material may be milled to obtain flakes or ribbons, and, if desired, .plodded in the usual manner using conventional soap-making machinery to form bars or cakes which have a characteristic translucent appearance.
Various adjuvant materials may be employed in the gel compositions of the present invention. Such materials may include perfume, coloring material, germicide and the like.
The following examples are additionally illustrative of the nature of the present invention and it will be understood that the invention is not limited thereto. All amounts or proportions are by weight unless otherwise indicated.
EXAMPLE I Table Percent H Soap: Non-Ionic Physical State 63 Liquid.
62 Twlo phases-small gel over liquid p ase.
61 Two phaseslarge gel over small liquid phase.
58 Solid gel.
Do. 45 Mobile gel. 38 Liquid. Do. 16 Do.
It will be apparent from the table that within certain approximate proportions of soap to non-ionic detergent in a ratio from about 4:1 to 1:12, the proportion of water being about 40% to 60%, the product is in the form of a gel. The solid gels which are obtained where the amount of soap to non-ionic detergent is about 4:1 to about 1:1 by weight are preferred for general use. Where there is indicated in the above table, the presence of a gel phaseover a liquid phase, such gel layer may be separated from the liquid phase in any suitable manner, such as by decantation.
EXAMPLE II 131 parts of the 36% potassium soap solution used in Example I are admixed with 44 parts of the Igepal CA with stirring, resulting in the obtention of a heavy White gel solid having approximately non-ionic, 27% anhydrous soap and 48% water. This gel exhibits good foaming and detersive properties.
EXAMPLE III parts of roll-dried potassium soaps of coconut fatty acid and red oil in a 3:1 ratio are admixed with 53 parts water and 16.6 parts Igepal CA with stirring, resulting in the formation of a solid gel. This gel exhibits satisfactory washing power.
EXAMPLE IV 800 parts of white flaked soap comprising a mixture of sodium salts of fatty acids derived from 75% coconut oil and 25% tallow fatty acids are admixed with 720 parts of water. This aqueous soap mixture is heated to 150 F. and 200 parts of the Igepal CA are added thereto. The resulting mixture is heated at 150 F. with stirring for 15 minutes and then it was allowed to cool to a gel. The gelled mixture exhibits satisfactory washing properties. A portion of the gel is dried to equilibrium moisture, milled to form shiny transparent-like flakes which are plodded to produce a detergent bar having a translucent appearance.
EXAMPLE V parts of the 36% potassium soap solution of Example I are mixed with 10 parts of a condensate of tall oil with 16-20 ethylene oxide groups, resulting in the formation'of a gel. This gel had about 10% non-ionic detergent, 32% soap and 58% water, and exhibits satisfactory detersive and foaming power also.
The admixture of parts of the soap solution to 5 parts of the non-ionic detergent results in an essentially liquid system having 5% non-ionic, 34% soap and 61% Water. In addition the admixture of 50 parts non-ionic to 50 parts of the soap solution results in a completely liquid system also having 50% non-ionic, 18% soap and water as the balance.
Although the present invention has been described and illustrated with a reference to specific examples, it is understood that modifications and variations of composition and procedure are contemplated within the scope of the appended claims.
Having thus described the said invention, what is claimed is:
1. A detergent composition in the form of a gel having a relatively dry form and consisting essentially of watersoluble alkali metal higher fatty acid soap, water-soluble non-ionic liquid higher alkyl phenol-ethylene oxide detergent having about 8 to 18 moles of ethylene oxide and water, said soap being derived from a mixture of about 75 coconut oil fatty acids and 25 fatty acid selected from the group consisting of oleic acid and tallow fatty acids, the amount of said soap and non-ionic detergent being from about 40 to about 60% by weight of said gel and in a ratio from about 4:1 to about 1:12 by weight.
2. A detergent composition in the form of a gel having a relatively dry form and consisting essentially of watersoluble potassium higher fatty acid soap, water-soluble non-ionic liquid higher alkyl phenol-ethylene oxide detergent having about 8 to 18 moles of ethylene oxide and water, said soap being derived from a mixture of, about 75 coconut oil fatty acids and 25 fatty acid selected from the group consisting of oleic acid and tallow fatty acids, the amount of said soap and non-ionic detergent being from about 40 to about 60% of said gel and in a ratio from about 4:1 to about 1:1 by Weight.
3. A detergent composition in the form of a gel having a relatively dry form and consisting essentially of watersoluble sodium higher fatty acid soap, water-soluble nonionic higher alkyl phenol-ethylene oxide detergent having about 8 to 18 moles of ethylene oxide and water, said soap being derived from a mixture of about 75 coconut oil fatty acids and 25 fatty acid selected from the group consisting of oleic acid and tallow fatty acids, the amount of said soap and non-ionic detergent being from about 40 to about 60% of said gel and in a ratio from about 4:1 to about 1:1 by weight.
4. A detergent composition in the form of a gel havin a relatively dry form and consisting essentially of watersoluhle higher fatty acid soap, water-soluble non-ionic liquid polyoxyethylene esters of tall oil detergent having about 12 to about 30 moles of ethylene oxide and water, said soap being derived from a mixture of about 75% coconut oil fatty acids and 25 fatty acid selected from the group consisting of-Loleic acid and tallow fatty acids, the amount of said soap and non-ionic detergent being from about 40 to about 60% by weight of said gel and the ratio from about 4:1 to about 1:1.2 by weight.
5. -A detergent composition in the form of a gel having a. relatively dry form and consisting essentially of watersoluble higher fatty acid soap, water and water-soluble non-ionic normally liquid polyalkylene oxide detergent selected from the group consisting of polyoxyalkylene condensates of higher alkyl phenol and polyoxyalkylene esters of higher fatty acids, said soap being derived from a mixture of about 75% coconut oil fatty acids and 25% fatty acid selected from the group consisting of oleic acid and tallow fatty acids, and said non-ionic detergent containing from 5 to 50 moles of alkylene oxide of 2 to 4 carbon atoms each, the amount of said soap and nonionic detergent being from about 40 to about 60% by weight and in a ratio from about 4:1 to 1:1.2 by weight.
References Cited in the file of this patent UNITED STATES PATENTS 2,084,632 Ellis June 22, 1937 2,543,744 Fox Mar. 6, 1951 FOREIGN PATENTS 697,510 Great Britain Sept. 23, 1953 OTHER REFERENCES

Claims (1)

  1. 5. A DETERGENT COMPOSITION IN THE FORM OF A GEL HAVING A RELATIVELY DRY FORM AND CONSISTING ESSENTIALLY OF WATERSOLUBLE HIGHER FATTY ACID SOAP, WATER AND WATER-SOLUBLE NON-IONIC NORMALLY LIQUID POLYALKYLENE OXIDE DETERGENT SELECTED FROM THE GROUP CONSISTING OF POLYOXALKYLENE CONDENSATES OF HIGHER ALKYL PHENOL AND POLYOXYALKYLENE ESTERS OF HIGHER FATTY ACIDS, SAID SOAP BEING DERIVED FROM A MIXTURE OF ABOUT 75% COCONUT OIL FATTY ACIDS AND 25% FATTY ACID SELECTED FROM THE GROUP CONSISTING OF OLEIC ACID AND TALLOW FATTY ACIDS, AND SAID NON-IONIC DETERGENT CONTAINING FROM 5 TO 50 MOLES OF ALKYLENE OXIDE OF 2 TO 4 CARBON ATOMS EACH, THE AMOUNT OF SAID SOAP AND NONIONIC DETERGENT BEING FROM ABOUT 40 TO ABOUT 60% BY WEIGHT AND IN A RATIO FROM ABOUT 4:1 TO 1:1.2 BY WEIGHT.
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3170915A (en) * 1960-04-11 1965-02-23 Monsanto Co Sucrose ethers
US3240819A (en) * 1960-02-17 1966-03-15 Monsanto Co Ethenoxy-substituted alkanols
US3528925A (en) * 1966-11-12 1970-09-15 Jacques Chapuis Encapsulated synthetic liquid detergent and process for preparing the same
US3907702A (en) * 1971-07-29 1975-09-23 Colgate Palmolive Co Process for making a free flowing soap-nonionic detergent
US3966628A (en) * 1974-08-21 1976-06-29 Westvaco Corporation Solid cleaning compositions containing C21 dicarboxylic acid
US4071475A (en) * 1975-09-16 1978-01-31 Kao Soap Co., Ltd. Transparent highly viscous liquid shampoo composition
US4130501A (en) * 1976-09-20 1978-12-19 Fmc Corporation Stable viscous hydrogen peroxide solutions containing a surfactant and a method of preparing the same
US4826632A (en) * 1986-10-20 1989-05-02 Lever Brothers Company Detergent compositions manufacturing process by spraying anionic/nonionic surfactant mix
US4975218A (en) * 1988-04-29 1990-12-04 Chesebrough-Ponds's USA Co. Aqueous soap composition containing ethoxylated nonionic surfactants
US5258136A (en) * 1992-03-04 1993-11-02 Application Chemicals, Inc. Alkoxylated compounds and their use in cosmetic stick formulations
US5443821A (en) * 1992-03-04 1995-08-22 Application Chemicals, Inc. Alkoxylated compounds and their use in cosmetic stick formulations

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2084632A (en) * 1933-04-25 1937-06-22 Standard Ig Co Hydrogenated naphtha soap gels and method of making same
US2543744A (en) * 1946-04-04 1951-03-06 Gen Aniline & Film Corp Nonfoaming soap composition
GB697510A (en) * 1950-09-28 1953-09-23 Celanese Corp Soap compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2084632A (en) * 1933-04-25 1937-06-22 Standard Ig Co Hydrogenated naphtha soap gels and method of making same
US2543744A (en) * 1946-04-04 1951-03-06 Gen Aniline & Film Corp Nonfoaming soap composition
GB697510A (en) * 1950-09-28 1953-09-23 Celanese Corp Soap compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3240819A (en) * 1960-02-17 1966-03-15 Monsanto Co Ethenoxy-substituted alkanols
US3170915A (en) * 1960-04-11 1965-02-23 Monsanto Co Sucrose ethers
US3528925A (en) * 1966-11-12 1970-09-15 Jacques Chapuis Encapsulated synthetic liquid detergent and process for preparing the same
US3907702A (en) * 1971-07-29 1975-09-23 Colgate Palmolive Co Process for making a free flowing soap-nonionic detergent
US3966628A (en) * 1974-08-21 1976-06-29 Westvaco Corporation Solid cleaning compositions containing C21 dicarboxylic acid
US4071475A (en) * 1975-09-16 1978-01-31 Kao Soap Co., Ltd. Transparent highly viscous liquid shampoo composition
US4130501A (en) * 1976-09-20 1978-12-19 Fmc Corporation Stable viscous hydrogen peroxide solutions containing a surfactant and a method of preparing the same
US4826632A (en) * 1986-10-20 1989-05-02 Lever Brothers Company Detergent compositions manufacturing process by spraying anionic/nonionic surfactant mix
US4923636A (en) * 1986-10-20 1990-05-08 Lever Brothers Company Detergent compositions
US4975218A (en) * 1988-04-29 1990-12-04 Chesebrough-Ponds's USA Co. Aqueous soap composition containing ethoxylated nonionic surfactants
US5258136A (en) * 1992-03-04 1993-11-02 Application Chemicals, Inc. Alkoxylated compounds and their use in cosmetic stick formulations
US5443821A (en) * 1992-03-04 1995-08-22 Application Chemicals, Inc. Alkoxylated compounds and their use in cosmetic stick formulations
WO1994022801A1 (en) * 1993-03-29 1994-10-13 Application Chemicals, Inc. Alkoxylated compounds and their use in cosmetic stick formulations

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