[go: up one dir, main page]

US3625905A - Detergent composition having softening properties - Google Patents

Detergent composition having softening properties Download PDF

Info

Publication number
US3625905A
US3625905A US684959A US3625905DA US3625905A US 3625905 A US3625905 A US 3625905A US 684959 A US684959 A US 684959A US 3625905D A US3625905D A US 3625905DA US 3625905 A US3625905 A US 3625905A
Authority
US
United States
Prior art keywords
detergent
composition according
salt
detergent composition
alkyl
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.)
Expired - Lifetime
Application number
US684959A
Inventor
Marvin C Weast
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.)
Purex Corp Ltd
Original Assignee
Purex Corp Ltd
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 Purex Corp Ltd filed Critical Purex Corp Ltd
Application granted granted Critical
Publication of US3625905A publication Critical patent/US3625905A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • 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
    • C11D10/045—Compositions 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
    • 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
    • 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
    • C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—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
    • C11D1/66—Non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds

Definitions

  • softening characteristics may be imparted to synthetic organic detergents by intimately mixing therewith a C saturated fatty acid or a water soluble salt thereof having a methyl substituted tertiary atom.
  • the intimate mixing may be accomplished by a codissolving the detergent and acid or salt in water and removing the water, e.g. in a conventional detergent spray drying apparatus.
  • a detergent and fabric softening composition which consists essentially of a mixture of noncationic synthetic organic detergent and the aforedescribed fatty acid or salt.
  • Commercially available C acids may be employed including those in which there may be present up to 60 weight percent acids or salts other than methyl branched C e.g. C to C saturated fatty acids or their salts.
  • a commercial saturated fatty acid of the formula C, H ,COOH comprising a complex mixture of isomers, primarily of the methyl branched series that are mutually soluble and only difficulty separable may be used.
  • the term C acid (or salt) is used herein to include such mixtures.
  • Anionic detergents are preferred herein, particularly alkyl sulfate and alkyl sulfonate anionic detergents such as alkali metal tallow alcohol sulfates and dodecyl benzene sulfonates e.g. sodium salts of the corresponding acids, and mixtures of these detergents. Proportions are not particularly critical with weight ratios of detergent to acid in the range of l:l to 0.5:l being suitable. Additives conventional in detergent formulation including, by way of illustration, builder salts, perfumes, optical brighteners, binders, et cetera, may also be employed.
  • the invention thus provides a method of softening fabrics during washing thereof with an aqueous washing solution of a synthetic organic detergent which includes introducing in the washing solution a C saturated fatty acid or water-soluble salt thereof having a methyl substituted tertiary carbon atom.
  • the essential components of the present inventive compositions are the synthetic organic detergent and the methyl branched C fatty acid or salt.
  • useful materials are the nonionic, amphoteric or anionic i.e. noncationic detergents.
  • suitable nonionic detergents include water-soluble nonionic polyalkylene oxide detergents such as are produced by the introduction of alkylene oxide group into an organic hydrophobic compound or group having an aliphtic or aromatic structure.
  • the hydrophobic organic group generally contains at least eight carbon atoms and up to about 30 carbon atoms. Condensed with the hydrophobic group are at least five and preferably up to about 50 alkylene oxide groups. It is preferred to use the polyoxyethylene condensates derived from ethylene oxide.
  • nonionic detergents it is preferred to use the polyalkylene oxide condensates of alkyl phenol, such as the polyoxyethylene ethers of alkyl phenols having a alkyl group of at least about six, and usually about eight to 12 carbons, and an ethylene oxide ratio (No. of moles per phenol) of about 7.5, 8.5, 1 1.5 and 20, through the number of ethylene oxide groups will be usually from about eight to 18.
  • alkyl substituent on the aromatic nucleus may be diisobutylene, diamyl, polymerized propylene, dimerized C -C olefin, and the like.
  • polyoxyalkylene esters of organic acids such as the higher fatty acids, rosin acids, tall oil acids, or acids from the oxidation of petroleum, et cetera.
  • These polyglycol esters will contain usually from about 12 to about 30 moles of ethylene oxide or its equivalent and about eight to 22 carbons in the acyl group.
  • Suitable products are refined tall oil condensed with 16 or 20 ethylene oxide groups, or similar polyglycol esters of lauric, stearic, oleic acids, etc.
  • Additional nonionic agents are the polyalkylene oxide condensates with higher fatty acid amides, such as the higher fatty acid primary amides, monoand di-ethanolamides.
  • Suitable agents are coconut fatty acid amide condensed with about 10 to 50 moles of ethylene oxide.
  • the fatty acyl group will have similarly about eight to 22 carbons, and usually about l0-to 18 carbon atoms, in such products.
  • the corresponding sulfonamides may be used also if desired.
  • polyether nonionic detergents are the polyalkylene oxide ethers of higher aliphatic alcohols.
  • Suitable fatty alcohols having a hydrophobic character, preferably eight to 22 carbons, are lauryl, myristyl, cetyl, stearyl and oleyl alcohols which may be condensed with an appropriate amount of ethylene oxide, such as at least about 6, and preferably about [0 to 30 moles.
  • a typical product is oleyl alcohol condensed with about l2, 15 or 20 moles of ethylene oxide.
  • the corresponding higher alkyl mercaptans or thioalcohols condensed with ethylene oxide are suitable in the present invention also.
  • the water-soluble polyoxyethylene condensates with hydrophobic polyoxypropylene glycols may be employed also.
  • nonionic detersive materials are the higher fatty acid alkanolamides, such as the monoethanolamides, diethanolamides and isopropanolamides wherein the acyl radical has about 10 to 14 carbon atoms and amine oxides.
  • Examples are coconut (or equivalent lauric), capric and myristic diethanolamide, monoethanolamide and isopropanolamide, dodecyl dimethyl amine oxide and dimethyl acetoxyalkylamine oxide where alkyl is C,,-C,,,.
  • suitable synthetic detergents are the anionic aromatic detergents, e.g. water-soluble higher alkyl aryl sulfonate detergents particularly those having from eight to about l8 carbon atoms in the alkyl group. It is preferred to use the higher alkyl benzene sulfonate detergent for optimum effects, though larly those having about eight to 18 carbons in the fatty alcohol residue, such as lauryl (or coconut fatty alcohol) sulfate and tallow alcohol sulfate.
  • Other suitable detergents are the sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids, e.g. oleic acid ester of isothionic acid; the higher fatty acid (e.g. cocanut ethanolamide sulfate, the higher fatty acid amide of amino alkyl sulfonic acids, e.g. lauric acid amide of taurine; and the like.
  • sulfate and sulfonate detergents are used in the form of their water-soluble salts, such as the alkali metal and nitrogen-containing, e.g. lower alkylolamine, salts.
  • alkali metal and nitrogen-containing e.g. lower alkylolamine
  • examples are the sodium, potassium, ammonium, isopropanolamine, monoand tri-ethanolamine salts of said higher alkyl benzene sulfonate, higher alkyl sulfate and the like.
  • the sodium salt of a sulfate ester of an alkylphenoxypoly (ethyleneoxy) ethanol the ammonium salt of this sulfate ester, sodium methyl oleyl taurate, sodium alkyl naphthalene sulfonate, alkyl acyl sodium sulfonate, sodium tetrahydronaphthalene sulfonate, sodium alkyl aryl sulfonate, alkyl amido sulfate, cocomonoglyceride sulfate, dodecylbenzene sodium sulfonate, dodecylbenzene sulfonic acid, tridecylbenzene sodium sulfonate, fatty alcohol sodium sulfate, sodium dodecyl diphenyl oxide disulfonate, sulfonated castor oil, polyethoxyalkyl phenol sulfonate triethanolamine salt, sodium tn'ethanolamine alkyl
  • noncationic materials such as amphoteric detergent materials can be employed in formulations having a pH above the materials isoelectric point including, illustratively, the sodium salt of N-coco beta amino propionate, N-lauryl beta amine propionic acid and metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates such as disclosed in USP 2,528,378 to Mannheimer.
  • the softeners herein found to be substantive to fabric through a detergent wash cycle and applicable during such cycle are generally the C saturated fatty acids and their water-soluble salts in which there occurs a methyl substituted tertiary carbon atom, in other words C fatty acids free of aliphatic unsaturation and having a branch chain.
  • Such acids have the formula:
  • R is a divalentorganic radical of l7 carbon atoms and Me is a methyl side chain located on any but the terminal carbon atom of R, which substituted carbon atom is thus a tertiary carbon atom.
  • Branch chain stearic acids having along the chain a methyl group side chain often termed isostearic acids" in the trade.
  • the methyl group position generally will vary with the acid source, particularly if a natural product e.g. degras or sheep wool fat.
  • Typical values for commercially available isostearic acids are:
  • Me R -c OOM derived from alkyl amines and alkanolamines e.g. from primary, secondary and tertiary alkyl amines such as mono-, di-, or tri-methyl, ethyl, propyl or butyl amines or primary, secondary and tertiary alkanol amines such as mono-, di-, or trimethanol, ethanol, propanol and isopropanol amines.
  • primary, secondary and tertiary alkyl amines such as mono-, di-, or tri-methyl, ethyl, propyl or butyl amines or primary, secondary and tertiary alkanol amines such as mono-, di-, or trimethanol, ethanol, propanol and isopropanol amines.
  • Proportions of synthetic organic detergent and C particular fatty acid or salt are not narrowly critical with as little as 0.5 part of the detergent per pan of the fatty acid/salt or 10 parts of detergent and 1 part of the acid/salt, by weight, being broadly useful in providing varying ranges of cleaning and softening action.
  • the weight ratio of synthetic organic detergent to fatty acid/salt will generally range between 5:1 and 1:1 with between 4:1 and 2:1 and especially the latter being particularly preferred when the mixture is blended with builder salts, as described below.
  • Builder salts are materials added to detergent formulations to assist in soil dispersion or suspension, deflocculation and water softening and to increase the alkalinity of the system. While suitable water-soluble inorganic salt may be employed commercially used materials are the alkali metal salts e.g. sodium, pottassium, lithium and cesium metal salts of phosphoric, sulfuric, carbonic or silicic acids. Typical materials include trisodium phosphate, tetrasodium phosphate, sodium tripolyphosphate, sodium sulfate, sodium carbonate, sodium silicate, potassium sulfate, phosphates, carbonates and silicates.
  • alkali metal salts e.g. sodium, pottassium, lithium and cesium metal salts of phosphoric, sulfuric, carbonic or silicic acids.
  • Typical materials include trisodium phosphate, tetrasodium phosphate, sodium tripolyphosphate, sodium sulfate, sodium carbonate, sodium silicate
  • Builder salts are employed in conventional amounts, e. g. 4: l to 1:1 by weight relative to the detergent, with weight ratios of 2:1 to 3:l being preferred.
  • a crutcher is charged with l sodium tallow alcohol sulfate, 10-20 percent by weight of the whole; (2) sodium tripolyphosphate, sodium sulfate, sodium silicate, (20-60 percent); (3) carboxymethylcellulose; (4) isostearic acid (-l0 percent); (5) sodium hydroxide (to neutralize the isostearic acid); brighteners and water to form a slurry of 50 percent solids.
  • the aqueous slurry is heated above F. and crutched until lump-free.
  • the slurry is then deaerated and spray-dried so that the resulting, easily dissolved, detergent beads have 5-10 percent moisture.
  • FABRIC WASHING PROCEDURE Fabric softening was tested by using terry cloths placed in a home-type automatic washing machine along with a load of naturally soiled fabrics. One cup of the spray-dried composition was added to the 15 gallon washer and set through the normal wash, rinse and spin-dry cycles. The wash load, including the test cloths, was dried in a home-type drier.
  • the two sets of coded cloths were evaluated by a panel of 10 persons who ranked the cloths according to softness. This procedure was repeated for 10 cycles. Using statistical optical methods, it was determined that the cloths washed in detergents with isostearic acid were significantly softer (at the 95 percent confidence level) than the cloths washed in the commercially-available detergent powder. The difference was noted from the first wash cycle through the th.
  • EXAMPLE 2 Sodium Tallow Alcohol Sulfate 20 parts Sodium tripolyphosphate 40 parts Sodium lsostearate 8-12 parts Sodium sulfate lS.S-l 1.5 pans Carboxymclhyl cellulose l.0 parts Optical Brighteners 0.5 parts Sodium silicate 5.0 parts Water 10.0 parts l00.0 parts EXAMPLE 3 Sodium Tallow Alcohol Sulfate 20 pans Sodium Tripolyphosphate 40 parts Potassium lsostearate 2 parts Sodium Sulfate 21.5 parts Carboxy methyl cellulose l.
  • the foregoing softening additive acids and salts may be blended with amine treated clays to enchance or compliment the fabric softening action.
  • compositions for imparting fabric softening characteristics to water soluble anionic, nonionic and amphoteric synthetic organic detergents which includes intimately mixing the detergent with an alkali metal salt of isotearic acid in a weight ratio of 0.5:l to 10:1 of detergent to said isostearic acid salt by codissolving the detergent and salt in water and removing the water from the mixture by heating.
  • Detergent composition having both fabric cleaning and softening characteristics, which consists essentially of a mixture of a detergent selected from the group consisting of water soluble anionic, nonionic and amphoteric synthetic organic detergents and an alkali metal salt of isostearic acid in a weight ratio of 0.5:1 to 10:] of detergent to said salt.
  • composition according to claim 3 in which said salt is an alkali metal salt selected from lithium, sodium and selected from the group consisting of potassium salts.
  • Detergent composition according to claim 3 including also C to C saturated fatty acids except C fatty acids in up to 60 weight percent of the total of fatty acids present in the composition.
  • said anionic detergent is an alkyl aryl sulfonate detergent in which the alkyl group contains from eight to 22 carbon atoms.
  • Detergent composition according to claim 8 in which said anionic detergent is alkyl benzene sulfonate.
  • Detergent composition according to claim 7 in which said anionic detergent is an alkyl sulfate in which the alkyl group contains from eight to 22 carbon atoms.
  • Detergent composition according to claim 10 in which said anionic detergent is tallow alcohol sulfate.
  • Detergent composition according to claim 3 in which said detergent includes both an alkyl sulfate and an alkyl aryl sulfonate detergent in which the alkyl groups each contain from eight to 22 carbon atoms.
  • Detergent composition according to claim 13 in which said alkyl sulfate is tallow alcohol sulfate and said alkyl aryl sulfonate is dodecyl benzene sulfonate.
  • Detergent composition according to claim 3 in which the weight ratio of said detergent to said salt is from S: l to l l l6.
  • Detergent composition according to claim 15 in which said detergent is a mixture of alkyl sulfate and alkyl aryl sulfonate detergents in which said alkyl groups each contain from eight to 18 carbon atoms and in proportions of 4:1 to 2:l by weight.
  • Detergent composition according to claim 3 in which there is additionally present from 20 to 60 percent by weight of a water-soluble inorganic builder salt in the total composition.
  • Method of softening fabrics during washing thereof with an aqueous washing solution of a synthetic organic noncationic detergent which includes introducing into the washing solution an alkali metal salt of isostearic acid in a weight ratio of 0.5:l to 10:] of detergent to said salt.

Landscapes

  • 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)

Abstract

Simultaneous cleansing and softening of fabrics is achieved by use of an aqueous solution of a mixture of synthetic organic noncationic detergent and an alkali metal salt of isostearic acid as the fabric wash water.

Description

United States Patent Inventor Marvin C. Weast Anaheim, Calif.
Appl. No. 684,959
Filed Nov. 22, 1967 Patented Dec. 7, 1971 Assignee Purex Corporation, Ltd.
Lakewood, Calil.
DETERGENT COMPOSITION HAVING SOFTENING PROPERTIES 19 Claims, No Drawings U.S. Cl 252/109, 252/8.7, 252/121, 252/138, 252/161 lnt.Cl Clld 9/10, Cl 1d 3/065 Field of Search 252/ 1 2 l 8.6, 8.7, 138, 109; 8/137, 142
References Cited UNITED STATES PATENTS 7/1969 Clark et al. 252/8.8
2,567,645 9/1951 Limburg 252/121 2,954,347 9/1960 St. John et a1. 252/109 2,527,329 10/1950 Powers et'al 117/1395 FOREIGN PATENTS 348,783 5/1931 Great Britain 252/8.6 640,373 7/1950 Great Britain.... 252/109 303,379 12/1928 Great Britain.... 252/8.6 431,964 7/1935 Great Britain... 252/8.6 737,824 10/1955 Great Britain 252/109 OTHER REFERENCES Marsh, J. T., An Introduction to Textile Finishing, 2d Edition, pp. 259- 266, Chapman & Hall Ltd., London 1948.
Primary Examiner- Leon D. Rosdol Assistant Examiner-P. E. Willis Attorney-White and Haefliger 7 salt of isostearic acid as the fabric wash water.
DETERGENT COMPOSITION HAVING SOFTENING PROPERTIES BACKGROUND OF THE INVENTION Field Of The Invention Synthetic organic detergents have found widespread use as cleaning materials for fabrics of all fibers. Numerous of these materials, including the most popular so-called heavy duty" detergents, which typically consist of an alkyl benzene sulfonate and a water soluble inorganic builder salt such a sodium tripolyphosphate, in aqueous wash solutions lend to fabrics a roughness or lack of hand" which is commercially disadvantageous.
It has been proposed to add after washing, with the final rinse, a softening agent such as l-methyl-1-alkylamidoethyl-2- alkylimidazolinium methosulfate. Since few automatic washing machines provide for automated introduction of this material, the housewife must stand by her automatic washer to add this softener product at the onset of the final rinse cycle. Toleration of this inconvenience merely illustrates the concern shown by consumers today for softness in washed fabrics.
SUMMARY OF THE INVENTION It is a major objective of the present invention to obviate critical sequential addition of laundry products with their attendant time waste and possible improper execution. In addition, it is an object to provide a single package laundry product which both washes and softens, in the same wash water, by a single addition. It is a further object to provide a softening product packageable with synthetic organic detergent and substantive to fabric through a detergent washing operation.
It has now been discovered that softening characteristics may be imparted to synthetic organic detergents by intimately mixing therewith a C saturated fatty acid or a water soluble salt thereof having a methyl substituted tertiary atom. The intimate mixing may be accomplished by a codissolving the detergent and acid or salt in water and removing the water, e.g. in a conventional detergent spray drying apparatus.
There results from this preparation a detergent and fabric softening composition which consists essentially of a mixture of noncationic synthetic organic detergent and the aforedescribed fatty acid or salt. Commercially available C acids may be employed including those in which there may be present up to 60 weight percent acids or salts other than methyl branched C e.g. C to C saturated fatty acids or their salts. For example, a commercial saturated fatty acid of the formula C, H ,COOH comprising a complex mixture of isomers, primarily of the methyl branched series that are mutually soluble and only difficulty separable may be used. The term C acid (or salt) is used herein to include such mixtures. Anionic detergents are preferred herein, particularly alkyl sulfate and alkyl sulfonate anionic detergents such as alkali metal tallow alcohol sulfates and dodecyl benzene sulfonates e.g. sodium salts of the corresponding acids, and mixtures of these detergents. Proportions are not particularly critical with weight ratios of detergent to acid in the range of l:l to 0.5:l being suitable. Additives conventional in detergent formulation including, by way of illustration, builder salts, perfumes, optical brighteners, binders, et cetera, may also be employed.
The invention thus provides a method of softening fabrics during washing thereof with an aqueous washing solution of a synthetic organic detergent which includes introducing in the washing solution a C saturated fatty acid or water-soluble salt thereof having a methyl substituted tertiary carbon atom.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The essential components of the present inventive compositions are the synthetic organic detergent and the methyl branched C fatty acid or salt.
With respect to the sythetic organic detergent, useful materials are the nonionic, amphoteric or anionic i.e. noncationic detergents.
In general, suitable nonionic detergents include water-soluble nonionic polyalkylene oxide detergents such as are produced by the introduction of alkylene oxide group into an organic hydrophobic compound or group having an aliphtic or aromatic structure. The hydrophobic organic group generally contains at least eight carbon atoms and up to about 30 carbon atoms. Condensed with the hydrophobic group are at least five and preferably up to about 50 alkylene oxide groups. It is preferred to use the polyoxyethylene condensates derived from ethylene oxide. Among the nonionic detergents, it is preferred to use the polyalkylene oxide condensates of alkyl phenol, such as the polyoxyethylene ethers of alkyl phenols having a alkyl group of at least about six, and usually about eight to 12 carbons, and an ethylene oxide ratio (No. of moles per phenol) of about 7.5, 8.5, 1 1.5 and 20, through the number of ethylene oxide groups will be usually from about eight to 18. The alkyl substituent on the aromatic nucleus may be diisobutylene, diamyl, 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, rosin acids, tall oil acids, or acids from the oxidation of petroleum, et cetera. These polyglycol esters will contain usually from about 12 to about 30 moles of ethylene oxide or its equivalent and about eight to 22 carbons in the acyl group. Suitable products are refined tall oil condensed with 16 or 20 ethylene oxide groups, or similar polyglycol esters of lauric, stearic, oleic acids, etc.
Additional nonionic agents are the polyalkylene oxide condensates with higher fatty acid amides, such as the higher fatty acid primary amides, monoand di-ethanolamides. Suitable agents are coconut fatty acid amide condensed with about 10 to 50 moles of ethylene oxide. The fatty acyl group will have similarly about eight to 22 carbons, and usually about l0-to 18 carbon atoms, in such products. The corresponding sulfonamides may be used also if desired.
Other suitable polyether nonionic detergents are the polyalkylene oxide ethers of higher aliphatic alcohols. Suitable fatty alcohols having a hydrophobic character, preferably eight to 22 carbons, are lauryl, myristyl, cetyl, stearyl and oleyl alcohols which may be condensed with an appropriate amount of ethylene oxide, such as at least about 6, and preferably about [0 to 30 moles. A typical product is oleyl alcohol condensed with about l2, 15 or 20 moles of ethylene oxide. The corresponding higher alkyl mercaptans or thioalcohols condensed with ethylene oxide are suitable in the present invention also. The water-soluble polyoxyethylene condensates with hydrophobic polyoxypropylene glycols may be employed also.
Further suitable nonionic detersive materials are the higher fatty acid alkanolamides, such as the monoethanolamides, diethanolamides and isopropanolamides wherein the acyl radical has about 10 to 14 carbon atoms and amine oxides. Examples are coconut (or equivalent lauric), capric and myristic diethanolamide, monoethanolamide and isopropanolamide, dodecyl dimethyl amine oxide and dimethyl acetoxyalkylamine oxide where alkyl is C,,-C,,,.
Other suitable synthetic detergents are the anionic aromatic detergents, e.g. water-soluble higher alkyl aryl sulfonate detergents particularly those having from eight to about l8 carbon atoms in the alkyl group. It is preferred to use the higher alkyl benzene sulfonate detergent for optimum effects, though larly those having about eight to 18 carbons in the fatty alcohol residue, such as lauryl (or coconut fatty alcohol) sulfate and tallow alcohol sulfate. Other suitable detergents are the sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids, e.g. oleic acid ester of isothionic acid; the higher fatty acid (e.g. cocanut ethanolamide sulfate, the higher fatty acid amide of amino alkyl sulfonic acids, e.g. lauric acid amide of taurine; and the like.
These sulfate and sulfonate detergents are used in the form of their water-soluble salts, such as the alkali metal and nitrogen-containing, e.g. lower alkylolamine, salts. Examples are the sodium, potassium, ammonium, isopropanolamine, monoand tri-ethanolamine salts of said higher alkyl benzene sulfonate, higher alkyl sulfate and the like. In commercial practice, it is preferred to use the alkali metal salts.
Typical specific examples are:
the sodium salt of a sulfate ester of an alkylphenoxypoly (ethyleneoxy) ethanol, the ammonium salt of this sulfate ester, sodium methyl oleyl taurate, sodium alkyl naphthalene sulfonate, alkyl acyl sodium sulfonate, sodium tetrahydronaphthalene sulfonate, sodium alkyl aryl sulfonate, alkyl amido sulfate, cocomonoglyceride sulfate, dodecylbenzene sodium sulfonate, dodecylbenzene sulfonic acid, tridecylbenzene sodium sulfonate, fatty alcohol sodium sulfate, sodium dodecyl diphenyl oxide disulfonate, sulfonated castor oil, polyethoxyalkyl phenol sulfonate triethanolamine salt, sodium tn'ethanolamine alkyl aryl sulfonate, magnesium lauryl sulfate, potassium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl ether sulfate, sodium tallow sulfate, dodecylbenzene sodium sulfonate, oleyl methyl tauride, ammonium lauryl sulfate, amide sulfonate, and the like.
Other noncationic materials such as amphoteric detergent materials can be employed in formulations having a pH above the materials isoelectric point including, illustratively, the sodium salt of N-coco beta amino propionate, N-lauryl beta amine propionic acid and metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates such as disclosed in USP 2,528,378 to Mannheimer.
The softeners herein found to be substantive to fabric through a detergent wash cycle and applicable during such cycle are generally the C saturated fatty acids and their water-soluble salts in which there occurs a methyl substituted tertiary carbon atom, in other words C fatty acids free of aliphatic unsaturation and having a branch chain. Such acids have the formula:
1 Me in which R is a divalentorganic radical of l7 carbon atoms and Me is a methyl side chain located on any but the terminal carbon atom of R, which substituted carbon atom is thus a tertiary carbon atom.
Branch chain stearic acids having along the chain a methyl group side chain often termed isostearic acids" in the trade. The methyl group position generally will vary with the acid source, particularly if a natural product e.g. degras or sheep wool fat. Typical values for commercially available isostearic acids are:
Molecular weight 284 Viscosity cps at 25C. 48 Acid Value l75 Titer C. 10 Iodine value ID The water-soluble salts of these acids may be used in addition to win place of all or part of the acid. In general, suitable salts are the alkali metal salts e.g. of the formula:
II Me R -c OOM derived from alkyl amines and alkanolamines e.g. from primary, secondary and tertiary alkyl amines such as mono-, di-, or tri-methyl, ethyl, propyl or butyl amines or primary, secondary and tertiary alkanol amines such as mono-, di-, or trimethanol, ethanol, propanol and isopropanol amines.
Proportions of synthetic organic detergent and C particular fatty acid or salt are not narrowly critical with as little as 0.5 part of the detergent per pan of the fatty acid/salt or 10 parts of detergent and 1 part of the acid/salt, by weight, being broadly useful in providing varying ranges of cleaning and softening action. in commercial formulations the weight ratio of synthetic organic detergent to fatty acid/salt will generally range between 5:1 and 1:1 with between 4:1 and 2:1 and especially the latter being particularly preferred when the mixture is blended with builder salts, as described below.
Builder salts are materials added to detergent formulations to assist in soil dispersion or suspension, deflocculation and water softening and to increase the alkalinity of the system. While suitable water-soluble inorganic salt may be employed commercially used materials are the alkali metal salts e.g. sodium, pottassium, lithium and cesium metal salts of phosphoric, sulfuric, carbonic or silicic acids. Typical materials include trisodium phosphate, tetrasodium phosphate, sodium tripolyphosphate, sodium sulfate, sodium carbonate, sodium silicate, potassium sulfate, phosphates, carbonates and silicates.
Builder salts are employed in conventional amounts, e. g. 4: l to 1:1 by weight relative to the detergent, with weight ratios of 2:1 to 3:l being preferred.
in the preparation of a typical formulation; a crutcher is charged with l sodium tallow alcohol sulfate, 10-20 percent by weight of the whole; (2) sodium tripolyphosphate, sodium sulfate, sodium silicate, (20-60 percent); (3) carboxymethylcellulose; (4) isostearic acid (-l0 percent); (5) sodium hydroxide (to neutralize the isostearic acid); brighteners and water to form a slurry of 50 percent solids.
The aqueous slurry is heated above F. and crutched until lump-free. The slurry is then deaerated and spray-dried so that the resulting, easily dissolved, detergent beads have 5-10 percent moisture.
in the examples all parts are by weight.
EXAMPLE 1 The following were blended and formed into detergent beads as above described:
Tallow Alcohol Sulfate 20 parts Sodium Tripolyphosphate 40 parts Sodium lsostearate 10 parts Sodium Sulfate l3.5 parts Carboxymethyl Cellulose 1. parts Optical Brighteners 0.5 parts Sodium Silicate 5.0 parts Water 10.0 parts l00.0 parts The isostearic acid used was a commercial grade known as Emery 3l0l-D lsostearic Acid containing a minimum of 40 percent by weight C acids.
FABRIC WASHING PROCEDURE Fabric softening was tested by using terry cloths placed in a home-type automatic washing machine along with a load of naturally soiled fabrics. One cup of the spray-dried composition was added to the 15 gallon washer and set through the normal wash, rinse and spin-dry cycles. The wash load, including the test cloths, was dried in a home-type drier.
CONTROL 1 For comparison, an identical load was washed using the leading detergent powder.
The two sets of coded cloths were evaluated by a panel of 10 persons who ranked the cloths according to softness. This procedure was repeated for 10 cycles. Using statistical optical methods, it was determined that the cloths washed in detergents with isostearic acid were significantly softer (at the 95 percent confidence level) than the cloths washed in the commercially-available detergent powder. The difference was noted from the first wash cycle through the th.
Other illustrative formulations include:
EXAMPLE 2 Sodium Tallow Alcohol Sulfate 20 parts Sodium tripolyphosphate 40 parts Sodium lsostearate 8-12 parts Sodium sulfate lS.S-l 1.5 pans Carboxymclhyl cellulose l.0 parts Optical Brighteners 0.5 parts Sodium silicate 5.0 parts Water 10.0 parts l00.0 parts EXAMPLE 3 Sodium Tallow Alcohol Sulfate 20 pans Sodium Tripolyphosphate 40 parts Potassium lsostearate 2 parts Sodium Sulfate 21.5 parts Carboxy methyl cellulose l. parts Optical Brighteners 0.5 parts Sodium Silicate 5.0 parts Water l0.0 parts l00.0 parts EXAMPLE 4 Sodium Tallow Alcohol Sulfate 20 parts Sodium Tripolyphosphate 40 parts Sodium lsostearate 20 parts Sodium Sulfate 3.5 parts Carboxy methyl cellulose 1. parts Optical Brighteners 0.5 parts Sodium Silicate 5.0 parts Water 10.0 parts l00.0 pans EXAMPLE 5 Sodium Dodecylbenzene sulfonute (anionic detergent) 67 parts Sodium lsostearute 33 parts EXAMPLE 6 Nonyl phenoxy polyethoxy ethane (non-ionic detergent) 67 pans Sodium lsostearatc 33 parts CONTROL ll Example 1 is duplicated using normal stearic acid. No statistically significant improvement over the control I is noted.
The foregoing softening additive acids and salts may be blended with amine treated clays to enchance or compliment the fabric softening action.
lclaim:
1. Method of preparing compositions for imparting fabric softening characteristics to water soluble anionic, nonionic and amphoteric synthetic organic detergents which includes intimately mixing the detergent with an alkali metal salt of isotearic acid in a weight ratio of 0.5:l to 10:1 of detergent to said isostearic acid salt by codissolving the detergent and salt in water and removing the water from the mixture by heating.
2. Method according to claim 1 in which the water is removed by spray drying the solution.
3. Detergent composition having both fabric cleaning and softening characteristics, which consists essentially of a mixture of a detergent selected from the group consisting of water soluble anionic, nonionic and amphoteric synthetic organic detergents and an alkali metal salt of isostearic acid in a weight ratio of 0.5:1 to 10:] of detergent to said salt.
4. Detergent composition according to claim 3 in which said salt is an alkali metal salt selected from lithium, sodium and selected from the group consisting of potassium salts.
5. Detergent composition according to claim 4 in which said salt is the sodium salt.
6. Detergent composition according to claim 3 including also C to C saturated fatty acids except C fatty acids in up to 60 weight percent of the total of fatty acids present in the composition.
7. Detergent composition according to claim 3 in which said detergent is an anionic detergent.
8. Detergent composition according to claim 7 in which said anionic detergent is an alkyl aryl sulfonate detergent in which the alkyl group contains from eight to 22 carbon atoms.
9. Detergent composition according to claim 8 in which said anionic detergent is alkyl benzene sulfonate.
l0. Detergent composition according to claim 7 in which said anionic detergent is an alkyl sulfate in which the alkyl group contains from eight to 22 carbon atoms.
11. Detergent composition according to claim 10 in which said anionic detergent is tallow alcohol sulfate.
12. Detergent composition according to claim 3 in which said detergent is nonionic.
13. Detergent composition according to claim 3 in which said detergent includes both an alkyl sulfate and an alkyl aryl sulfonate detergent in which the alkyl groups each contain from eight to 22 carbon atoms.
14. Detergent composition according to claim 13 in which said alkyl sulfate is tallow alcohol sulfate and said alkyl aryl sulfonate is dodecyl benzene sulfonate.
15. Detergent composition according to claim 3 in which the weight ratio of said detergent to said salt is from S: l to l l l6. Detergent composition according to claim 15 in which said detergent is a mixture of alkyl sulfate and alkyl aryl sulfonate detergents in which said alkyl groups each contain from eight to 18 carbon atoms and in proportions of 4:1 to 2:l by weight.
17. Detergent composition according to claim 3 in which there is additionally present from 20 to 60 percent by weight of a water-soluble inorganic builder salt in the total composition.
18. Method of softening fabrics during washing thereof with an aqueous washing solution of a synthetic organic noncationic detergent which includes introducing into the washing solution an alkali metal salt of isostearic acid in a weight ratio of 0.5:l to 10:] of detergent to said salt.
19. Method according to claim 18 in which the weight ratio of detergent to isostearic acid salt in said solution is between 5:1 and 1:1.

Claims (18)

  1. 2. Method according to claim 1 in which the water is removed by spray drying the solution.
  2. 3. Detergent composition having both fabric cleaning and softening characteristics, which consists essentially of a mixture of a detergent selected from the group consisting of water soluble anionic, nonionic and amphoteric synthetic organic detergents and an alkali metal salt of isostearic acid in a weight ratio of 0.5:1 to 10:1 of detergent to said salt.
  3. 4. Detergent composition according to claim 3 in which said salt is an alkali metal salt selected from the group consisting of lithium, sodium and potassium salts.
  4. 5. Detergent composition according to claim 4 in which said salt is the sodium salt.
  5. 6. Detergent composition according to claim 3 including also C14 to C22 saturated fatty acids except C18 fatty acids in up to 60 weight percent of the total of fatty acids present in the composition.
  6. 7. Detergent composition according to claim 3 in which said detergent is an anionic detergent.
  7. 8. Detergent composition according to claim 7 in which said anionic detergent is an alkyl aryl sulfonate detergent in which the alkyl group contains from eight to 22 carbon atoms.
  8. 9. Detergent composition according to claim 8 in which said anionic detergent is alkyl benzene sulfonate.
  9. 10. Detergent composition according to claim 7 in which said anionic detergent is an alkyl sulfate in which the alkyl group contains from eight to 22 carbon atoms.
  10. 11. Detergent composition according to claim 10 in which said anionic detergent is tallow alcohol sulfate.
  11. 12. Detergent composition according to claim 3 in which said detergent is nonionic.
  12. 13. Detergent composition according to claim 3 in which said detergent includes both an alkyl sulfate and an alkyl aryl sulfonate detergent in which the alkyl groups each contain from eight to 22 carbon atoms.
  13. 14. Detergent composition according to claim 13 in which said alkyl sulfate is tallow alcohol sulfate and said alkyl aryl sulfonate is dodecyl benzene sulfonate.
  14. 15. Detergent composition according to claim 3 in which the weight ratio of said detergent to said salt is from 5:1 to 1:1.
  15. 16. Detergent composition according to claim 15 in which said detergent is a mixture of alkyl sulfate and alkyl aryl sulfonate detergents in which said alkyl groups each contain from eight to 18 carbon atoms and in proportions of 4:1 to 2:1 by weight.
  16. 17. Detergent composition according to claim 3 in which there is additionally present from 20 to 60 percent by weight of a water-soluble inorganic builder salt in the total composition.
  17. 18. Method of softening fabrics during washing thereof with an aqueous washing solution of a synthetic organic noncationic detergent which includes introducing into the washing solution an alkali metal salt of isostearic acid in a weight ratio of 0.5:1 to 10:1 of detergent to said salt.
  18. 19. Method according to claim 18 in which the weight ratio of detergent to isostearic acid salt in said solution is between 5:1 and 1:1.
US684959A 1967-11-22 1967-11-22 Detergent composition having softening properties Expired - Lifetime US3625905A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US68495967A 1967-11-22 1967-11-22

Publications (1)

Publication Number Publication Date
US3625905A true US3625905A (en) 1971-12-07

Family

ID=24750216

Family Applications (1)

Application Number Title Priority Date Filing Date
US684959A Expired - Lifetime US3625905A (en) 1967-11-22 1967-11-22 Detergent composition having softening properties

Country Status (1)

Country Link
US (1) US3625905A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852211A (en) * 1972-08-09 1974-12-03 Procter & Gamble Detergent compositions
US4062647A (en) * 1972-07-14 1977-12-13 The Procter & Gamble Company Clay-containing fabric softening detergent compositions
US4418011A (en) * 1982-08-03 1983-11-29 Colgate-Palmolive Company Detergent composition providing antistatic properties
US4421514A (en) * 1982-08-03 1983-12-20 Colgate-Palmolive Antistatic laundry treatment
US4430236A (en) 1981-06-22 1984-02-07 Texize, Division Of Mortonthiokol Liquid detergent composition containing bleach
US4436637A (en) 1982-12-13 1984-03-13 Colgate-Palmolive Company Fabric softening heavy duty liquid detergent containing a mixture of water insoluble soap and clay
EP0296431A3 (en) * 1987-06-25 1990-12-05 Kao Corporation Use of a branched carboxylic acid as additive for an alkaline detergent composition for cleaning metallic articles in an electrolytic cleaning operation
WO1993005760A1 (en) * 1991-09-24 1993-04-01 Henkel Kommanditgesellschaft Auf Aktien Aqueous, clear liquid concentrates of alkyle sulfates
US5584858A (en) * 1994-11-14 1996-12-17 United States Surgical Corporation Tubing fluid
US5698511A (en) * 1994-12-05 1997-12-16 Colgate-Palmolive Company Granular detergent compositions containing deflocculating polymers and process for preparing such compositions
DE10144051A1 (en) * 2001-09-07 2002-12-05 Sasol Germany Gmbh Surfactant composition, e.g. useful as hard surface cleaner or textile auxiliary, comprises branched carboxylic acid salt and optionally alkoxylated and/or sulfated primary alcohol
WO2005017086A1 (en) * 2003-08-18 2005-02-24 Unilever Plc Detergent composition
US6864196B2 (en) 1995-12-19 2005-03-08 Newlund Laboratories, Inc. Method of making a laundry detergent article containing detergent formulations
US12215302B1 (en) 2024-06-28 2025-02-04 Bala Nathan Smectite clay-based fabric softener compositions with etheramine stabilizers

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB303379A (en) *
GB348783A (en) * 1929-04-20 1931-05-21 Hermann Bollmann Improvements in and relating to the treatment of textile materials or the like
GB431964A (en) * 1933-07-03 1935-07-18 British Celanese Improvements in dressings for textile materials
GB640373A (en) * 1947-06-26 1950-07-19 Henry Fraser Johnson An improved soap composition and method of making the same
US2527329A (en) * 1944-07-26 1950-10-24 Monsanto Chemicals Method for producing slip-resistant textile materials
US2567645A (en) * 1947-05-16 1951-09-11 Shell Dev Process of producing a detergent composition
GB737824A (en) * 1953-06-09 1955-10-05 Henry Fraser Johnston An improved detergent composition and method of making same
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US3454494A (en) * 1965-08-03 1969-07-08 Standard Chem Products Inc Textile softener compositions

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB303379A (en) *
GB348783A (en) * 1929-04-20 1931-05-21 Hermann Bollmann Improvements in and relating to the treatment of textile materials or the like
GB431964A (en) * 1933-07-03 1935-07-18 British Celanese Improvements in dressings for textile materials
US2527329A (en) * 1944-07-26 1950-10-24 Monsanto Chemicals Method for producing slip-resistant textile materials
US2567645A (en) * 1947-05-16 1951-09-11 Shell Dev Process of producing a detergent composition
GB640373A (en) * 1947-06-26 1950-07-19 Henry Fraser Johnson An improved soap composition and method of making the same
GB737824A (en) * 1953-06-09 1955-10-05 Henry Fraser Johnston An improved detergent composition and method of making same
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US3454494A (en) * 1965-08-03 1969-07-08 Standard Chem Products Inc Textile softener compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Marsh, J. T., An Introduction to Textile Finishing, 2d Edition, pp. 259 266, Chapman & Hall Ltd., London 1948. *

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4062647A (en) * 1972-07-14 1977-12-13 The Procter & Gamble Company Clay-containing fabric softening detergent compositions
US3852211A (en) * 1972-08-09 1974-12-03 Procter & Gamble Detergent compositions
US4430236A (en) 1981-06-22 1984-02-07 Texize, Division Of Mortonthiokol Liquid detergent composition containing bleach
CH670543GA3 (en) * 1982-08-03 1989-06-30
US4421514A (en) * 1982-08-03 1983-12-20 Colgate-Palmolive Antistatic laundry treatment
FR2531450A1 (en) * 1982-08-03 1984-02-10 Colgate Palmolive Co DETERGENT COMPOSITIONS PROVIDING ANTISTATIC PROPERTIES
FR2531462A1 (en) * 1982-08-03 1984-02-10 Colgate Palmolive Co TREATMENT OF LAUNDRY AGAINST STATIC ELECTRICITY
US4418011A (en) * 1982-08-03 1983-11-29 Colgate-Palmolive Company Detergent composition providing antistatic properties
US4436637A (en) 1982-12-13 1984-03-13 Colgate-Palmolive Company Fabric softening heavy duty liquid detergent containing a mixture of water insoluble soap and clay
EP0296431A3 (en) * 1987-06-25 1990-12-05 Kao Corporation Use of a branched carboxylic acid as additive for an alkaline detergent composition for cleaning metallic articles in an electrolytic cleaning operation
WO1993005760A1 (en) * 1991-09-24 1993-04-01 Henkel Kommanditgesellschaft Auf Aktien Aqueous, clear liquid concentrates of alkyle sulfates
US5584858A (en) * 1994-11-14 1996-12-17 United States Surgical Corporation Tubing fluid
US5698511A (en) * 1994-12-05 1997-12-16 Colgate-Palmolive Company Granular detergent compositions containing deflocculating polymers and process for preparing such compositions
US6864196B2 (en) 1995-12-19 2005-03-08 Newlund Laboratories, Inc. Method of making a laundry detergent article containing detergent formulations
DE10144051A1 (en) * 2001-09-07 2002-12-05 Sasol Germany Gmbh Surfactant composition, e.g. useful as hard surface cleaner or textile auxiliary, comprises branched carboxylic acid salt and optionally alkoxylated and/or sulfated primary alcohol
WO2005017086A1 (en) * 2003-08-18 2005-02-24 Unilever Plc Detergent composition
US20050043201A1 (en) * 2003-08-18 2005-02-24 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Detergent composition
US12215302B1 (en) 2024-06-28 2025-02-04 Bala Nathan Smectite clay-based fabric softener compositions with etheramine stabilizers

Similar Documents

Publication Publication Date Title
US3625905A (en) Detergent composition having softening properties
FI61043B (en) UPPMJUKNINGSKOMPOSITIONER FOER TYGER
US3983079A (en) Dishwashing composition
US3694364A (en) Laundering aid
US4153570A (en) Low-foaming liquid washing agent concentrates
EP0666308B1 (en) Multi-purpose liquid cleaning compositions
US3351483A (en) Method of softening textile fabrics
NO144268B (en) DETERGENT.
JP2004536197A (en) Liquid softener and textile washing method
JPS6335699A (en) Detergent composition having clothing softening property
EP0023361A1 (en) Laundry detergent containing anti-redeposition agent
EP0013585A1 (en) Light duty liquid detergent composition
WO2011114876A1 (en) Liquid detergent composition
US10266791B2 (en) Detergent compositions
US3859225A (en) Drycleaning detergent composition
US4225471A (en) Cleaning composition containing mineral spirits alkanolamide, and oleyl dimethylamine oxide
US3776851A (en) Detergents containing tetrahydroxysuccinic acid and salts thereof
JPH021800A (en) Fabrics softening additive for detergent composition
US3676341A (en) Textile softening compositions
WO2018139389A1 (en) Liquid detergent composition
EP3458565A1 (en) Pre-treatment composition for fabric stains
FI58937B (en) LAOGLOEDDRANDE TVAETTMEDELSKOMPOSITIONER
JPH09250079A (en) Cleaning of textile product
KR910004890B1 (en) Detergent composition with fabric softening properties
SE412598B (en) LIQUID DETERGENT COMPOSITION WITH POWERFUL WASHING EFFECT