US3709836A - Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same - Google Patents

Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same Download PDF

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Publication number
US3709836A
US3709836A US00041602A US3709836DA US3709836A US 3709836 A US3709836 A US 3709836A US 00041602 A US00041602 A US 00041602A US 3709836D A US3709836D A US 3709836DA US 3709836 A US3709836 A US 3709836A
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amine
composition according
percent
detergent
fatty acid
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Expired - Lifetime
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US00041602A
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English (en)
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J Inamorato
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Colgate Palmolive Co
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Colgate Palmolive Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds

Definitions

  • Foaming, or sudsing, of detergents is an extremely important factor to consider when formulating a detergent composition. It is known, for example, that a detergent which over-foams does not do an efficient job of cleaning in a washing machine. On the other hand, in hand washing there is a desire on the part of most consumers for a substantial amount of foam produced by a detergent. It is therefore necessary to provide a detergent composition which produces enough foam to reassure the consumer but yet not so much foam as to inhibit the detergent action of the composition. This need has been satisfactorily achieved in many ways.
  • washing machines are designed with internal water heating systems which begin their cycle with cold water and gradually heat the same to the desired operating temperature which is usually the boil." Such washing machines are used extensively, for instance, in many European countries. It is well known, however, that a detergent system which provides an adequate level of foam when used with hot water will not foam at all in cold water. Conversely, a detergent system which is compounded so that a sufficient level of foam is produced in cold water will overfoam to the extent of overflowing the washing machine when used with hot water.
  • a composition for regulating the foam profile of a detergent system, comprising a binary synergistic mixture of a fatty acid and a high molecular weight primary, secondary or tertiary amine.
  • a detergent composition having an inverse foamto-temperature relationship which comprises an anionic detergent, inorganic builders, and a synergistic mixture of a fatty acid and a high molecular weight primary, secondary or tertiary amine.
  • the detergent composition could have other additives such as brighteners, germici des, soil suspending agents, antioxidants, bleaches, coloring materials, and perfume. lt is quite unexpected to find that the mixture ofa fatty acid and an amine provides the inverse foamto-temperature relationship, since each of the ingredients, when used alone, do not exhibit any such properties.
  • the useful fatty acids which may be employed in the present invention include those saturated linear acids containing between about eight and 30 carbon atoms in their alkyl chain. These'include:
  • the preferred fatty acids are those having alkyl chains of from about 14 to 22 carbon atoms.
  • One such preferred fatty acid is stearic acid.
  • Another preferred acid composition is available commercially under the name Hyfac 431.
  • Hyfac 431 is a hydrogenated fish fatty acid having the following approximate composition:
  • Hystrene 7022 comprises about 70 percent C to C fatty acids.
  • Hystrene 9022 comprises about 90 percent C to C fatty acids, and Hystre'ne 9018 has about 90 percent stearic acid.
  • Neofat 18-58 is a hydrogenated tallow acid.
  • Kemamine The fatty acid, used in comthe name Kemamine. Representative of these are:
  • the useful detergents which may be used in conjunction with the foam profile regulating composition of the present invention include anionic detergents such as alkylbenzene-sulfonic acid and its salts, and compounds of the formula alkyl-phenyl-'SO M, wherein alkyl is an alkyl radical of a fatty acid and M is hydrogen or an alkali metal, which compounds comprise a well-known class of anionic detergents and include sodium dodecyl-benzene sulfonate, potassium dodecylbenzenesulfonate.
  • anionic detergents such as alkylbenzene-sulfonic acid and its salts
  • compounds of the formula alkyl-phenyl-'SO M wherein alkyl is an alkyl radical of a fatty acid and M is hydrogen or an alkali metal, which compounds comprise a well-known class of anionic detergents and include sodium dodecyl-benzene sulfonate, potassium dodecylbenzenesulfonate
  • alkali metal dialkyl sulfosuccinates e.g., sodium dioctylsulfosuccinate, and sodium dihexylsulfosuccinate, sodium sulfoethylphthalate, sodium lauryl-p-anisidinesulfonate; sodium tetradecanesulfonate; sodium diisopropylnapthalenesulfonate; sodium octylphenoxyethoxyethylsulfonate, etc.; and the alkali metal alkyl sulfates,
  • alkylbenzene-sulfonic acid and salts thereof included those which. are biodegradable and which are particularly characterized by a linear alkyl substituent of from C to C and preferably from C to C It is, of course,
  • substantially pure olefins as well as alkylating compounds used in other techniques can and do give alkylated benzene sulfonates wherein the alkyl moiety is substantially (i.e., at least 99 percent) of one chain length; i.e., C C C or C.
  • the linear alkyl benzene sulfonates are further characterized by the position of the'benzene ring in the linear alkyl chain, with any of the position isomers (i.e., alpha to omega) being operable and contemplated.
  • linear alkyl benzene sulfonates are generally and conveniently prepared by sulfonating the corresponding alkyl benzene hydrocarbons which in turn may be prepared by alkylating benzene with a linear alkyl halide, a l-alkene or a linear primary or secondary alcohol.
  • Pure isomers (of the l-phenyl isomer) are prepared by reduction of the acylated benzene (alkyl phenyl ketone) using a modification of the Wolff- Keshner reaction.
  • the 2-phenyl' isomer is obtained from n-undecyl phenyl ketone and methyl magnesium bromide to form the tertiary alcohol which is dehydrated to the alkene and then hydrogenated.
  • the 5-phenyl isomer is obtained similarly from a n-heptyl phenyl ketone and n-butyl magnesium bromide.
  • the other isomers are obtainedin a similar manner from the appropriate n-alkyl phenyl ketone and n-alkyl magnesium bromide.
  • benzene sulfonates In addition to the benzene sulfonates, one may also employ the lower alkyl (C, to C analogs of benzene such as toluene, xylene, the trimethyl benzenes, ethyl benzene, isopropyl benzene, and the like.
  • the sulfonates are generally employed in the water soluble salt form which includes as the cation the alkali metals, ammonium, and lower amine and alkanolamine.
  • anionic detergents are the olefin sulfonates including long chain alkene sulfonates, long chain hydroxyalkan'e sulfonates or mixtures of alkensulfonates and hydroxyalkanesulfonates.
  • linear paraffin sulfonates are also a well-known group of compounds and include water soluble salts (alkali metal, amine, alkanolamine, and ammonium) of: I
  • the linear alkyl sulfates which are contemplated in this invention comprise the range of C to C Specific examples include sodium n-decyl sulfate; sodium ndodecyl sulfate; sodium n-octadecyl sulfate; and the exthoxylated (l to 100 moles ethylene oxide) derivatives; and, of course, the other water soluble salt-forming cations mentioned above.
  • composition of the present invention may also include in addition to the foam profile regulating compounds and conventional anionic detergent compositions builders, brighteners, hydrotropes, germicides, soil suspending agents, anti-redeposition agents, antioxidants, bleaches, coloring materials (dyes and pigments), perfumes, water soluble alcohols, non-deterabout 1 to 6 percent fatty acid and from about 1 to about 6 percent amine; and preferably from about 2 to 5 percent fatty acid and from about 1 to about 3 percent amine. All of said percentages are by weight, based on the total amount of the composition being used. In the case of the detergent systems, the percentages are based on an anionic detergent concentration of about 8 to 18 percent by weight.
  • the amount of builder or mixture of builder salts may range from ID to 85 pergent alkali metal benzene sulfonates, fabric softening compounds, enzymes, etc.
  • the builder is, generally, a water soluble, inorganic salt which may be a neutral salt, e.g., sodium sulfate or an alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • a neutral salt e.g., sodium sulfate or an alkaline builder salt
  • phosphates, silicates, bicarbonates, carbonates, and borates e.g., sodium sulfate or an alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • alkaline builder salt such as phosphates, silicates, bicarbonates, carbonates, and borates.
  • the preferred builders are those characterized as condensed phosphates such as polyphosphates and pyrophosphates.
  • alkaline salts are: tetrasodium pyrophosphates, pentasodium tripolyphosphate (either Phase I or Phase II), sodium hexametaphosphate, and the corresponding potassium salts of these compounds, sodium and potassium silicates, e.g., sodium metasilicate and alkaline silicates (Na O; 2Si0 and Na O; 3SiO sodium carbonate, potassium carbonate and sodium and potassium bicarbonate.
  • Other salts may also be used where the compounds are water soluble. These include the general class of alkali metal, alkaline earth metal, amine, alkanolamine, and ammonium salts.
  • Other builders which are salts of organic acids may also be used, and in particular the water soluble (alkali metal, ammonium, substituted ammonium and amine) salts of aminopolycarboxylic acids such as:
  • ethylene diamine tetra-acetic acid nitrilo triacetic acid diethylene triamine penta-acetic acid N-(2-hydroxyethyl)-ethylene diamine acid 2hydroxyethyl-iminodiacetic acid 1,2-diaminocyclohexane diacetic acid, and the like.
  • hydrotropes include such compounds as sodium triacetic xylene sulfonate, potassium xylene sulfonate, sodium and potassium toluene sulfonates, in the position isomers thereof, and ethyl benzene sulfonate.
  • composition for regulating the foam profile of a detergent there is employed from about 20 to 90 percent fatty acid and from about 10 to about 80 percent amine. Preferably, there employed from about 35 to 60 percent fatty acid and from about 20 to about 40 percent amine. In terms of the total detergent system, there is employed from cent by weight.
  • the following examples demonstrate the foam profiles of various detergent systems under the conditions of use to be encountered in Europe.
  • the detergent compositions were tested in. a Miele automatic washing machine, which is of German manufacture.
  • the machine is a front-loading, tumbler type washing machine equipped with a heater that raises the water temperature from room temperature to the boil.
  • the machine operates on 200 volts, 5O cycle alternating current. In each instance, the machine was set on the white clothes setting, and a five-pound load of clean clothing was used. The water capacity if 1 1 liters.
  • a detergent concentration of 0.5 percent was used in each cycle. This detergent concentration was provided by using 56 grams of detergent.
  • the machine operates on two cycles, a pre-wash cycle and a wash cycle.
  • a pre-wash cycle the temperature of the water climbs from to F., and the total cycle is 12 to 14 minutes.
  • the drum rotates for about l0 seconds, rests for 4 seconds, reverses direction, and the operation is repeated.
  • the machine stops, drains, and remains motionless" unto the wash cycle starts.
  • the wash cycle is divided into two stages, the heating stage and the washing stage.
  • the heating stage cold water washes a second charge of detergent into the drum.
  • the temperature climbs from about 90F. to over F.
  • the drum rotates for 4 to 5 seconds, rests for l 0 seconds, reverses direction, and repeats the operation.
  • the machine changes its drum action and goes into the washing stage.
  • the washin g stage lasts 18 minutes. During this time, the drum action is the same as that described for the pre-wash cycle.
  • the temperature fluctuates between l90 and 200F. during the whole washing stage.
  • Example 2 is repeated employing the fatty acid mixture as a sodium soap in the following concentrations:
  • Example I formulation 3, is once more repeated except that the amine is varied as follows:
  • fatty acids or the like includes the corresponding water-soluble soaps thereof, preferably the alkali metal soaps such as sodium and potassium.
  • the fatty acids per se and soaps thereof may be used interchangeably depending upon economics, method of manufacture of the composition with other ingredients and its use in washing.
  • fatty acids may exist in the product when post-added to a detergent powder; or partly or wholly in the form of soap when added to a slurry or solution during manufacture of detergent products in the presence of alkaline materials or in alkaline washing solutions.
  • a detergent composition having an inverse foamto-temperature relationship consisting essentially of (1) from about I to 6 percent by weight of saturated linear fatty acid containing between about eight and 30 carbon atoms in the alkyl chain, (2) from about 1 to 6 percent by weight of primary, secondary or tertiary fatty amine having a saturated or unsaturated alkyl chain of from about 14 to 22 carbon atoms, and (3) from about 8 to 18 percent by weight of a built anionic detergent.
  • composition according to claim 1 wherein said anionic detergent is a linear alkyl benzene sulfonate having about eight to 22 carbon atoms in the alkyl group.
  • composition according to claim 2 wherein said alkyl group has about 10 to 15 carbon atoms.
  • composition according to claim 1 wherein said detergent is linear alkyl benzene sulfonate, and said builder salts are selected from the group consisting of alkali metal and ammonium polyphosphates, silicates, borates, sulfates, and combinations thereof.
  • composition according to claim 1 wherein said fatty acid contains from about 14 to 22 carbon atoms.
  • composition according to claim 5 wherein said fatty acid is hydrogenated fish fatty acid.
  • composition according to claim 5 wherein said fatty acid is a mixture of C to C fatty acids.
  • composition according to claim 1 wherein said fatty acid is present in from about 2 to 5 percent by weight of said composition.
  • composition according to claim 1 wherein said amine is a tertiary amine.
  • composition according to claim 9 wherein said amine is methyl bis-hydrogenated tallow amine.
  • tergent composition containing from about 8 to 18 percent by weight of detergent, from about 1 to 6 percent by weight of fatty acid and from about I to 6 percent by weight of fatty amine said foam profile composition consisting essentially of (1) from about 20 to 90 percent by weight of saturated, linear fatty acid containing between about eight and 30 carbon atoms in the alkyl chain and (2) from about 10 to percent by weight of primary, secondary or tertiary fatty amine having a saturated or unsaturated alkyl chain of from about 14 to 22 carbon atoms.

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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)
US00041602A 1970-05-28 1970-05-28 Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same Expired - Lifetime US3709836A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US4135870A 1970-05-28 1970-05-28
US4160170A 1970-05-28 1970-05-28
US4130870A 1970-05-28 1970-05-28
US4139270A 1970-05-28 1970-05-28
US4135970A 1970-05-28 1970-05-28
US4160270A 1970-05-28 1970-05-28

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Application Number Title Priority Date Filing Date
US00041602A Expired - Lifetime US3709836A (en) 1970-05-28 1970-05-28 Built anionic detergent composition having inverse foam-to-temperature relationship and process for producing same
US41308A Expired - Lifetime US3704267A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US00041601A Expired - Lifetime US3716499A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US41392A Expired - Lifetime US3696056A (en) 1970-05-28 1970-05-28 Ternary foam control systems with amines or amides and detergent compositions containing same
US00041358A Expired - Lifetime US3730912A (en) 1970-05-28 1970-05-28 Ternary foam control systems and detergent compositions containing same
US00041359A Expired - Lifetime US3714074A (en) 1970-05-28 1970-05-28 Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship

Family Applications After (5)

Application Number Title Priority Date Filing Date
US41308A Expired - Lifetime US3704267A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US00041601A Expired - Lifetime US3716499A (en) 1970-05-28 1970-05-28 Ternary foam control composition and built anionic detergent composition containing same
US41392A Expired - Lifetime US3696056A (en) 1970-05-28 1970-05-28 Ternary foam control systems with amines or amides and detergent compositions containing same
US00041358A Expired - Lifetime US3730912A (en) 1970-05-28 1970-05-28 Ternary foam control systems and detergent compositions containing same
US00041359A Expired - Lifetime US3714074A (en) 1970-05-28 1970-05-28 Foam profile regulating composition and anionic detergent composition containing same and having inverse foam to temperature relationship

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US (6) US3709836A (de)
AT (1) AT325182B (de)
BE (1) BE767873A (de)
CA (6) CA945034A (de)
CH (1) CH552053A (de)
DE (1) DE2126061A1 (de)
DK (1) DK138662B (de)
FR (1) FR2093742A5 (de)
GB (1) GB1286054A (de)
NL (1) NL7107442A (de)
SE (1) SE382464B (de)

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US3853779A (en) * 1972-06-06 1974-12-10 Colgate Palmolive Co Low foaming detergent compositions
US3920564A (en) * 1972-09-20 1975-11-18 Colgate Palmolive Co Softener-detergent composition
US4375416A (en) * 1978-11-20 1983-03-01 The Procter & Gamble Company Detergent composition having textile softening properties
US4744911A (en) * 1985-08-01 1988-05-17 The Procter & Gamble Company Dispersible fabric softeners
US5412825A (en) * 1991-10-21 1995-05-09 Samsung Electronics Co., Ltd. Top cover locking system of a boiling clothes washing machine

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US3893941A (en) * 1971-09-09 1975-07-08 Nalco Chemical Co Foam inhibiting composition
GB1412123A (en) * 1972-01-28 1975-10-29 Unilever Ltd Detergent composition
DE2213557A1 (de) * 1972-03-12 1973-09-27 Henkel & Cie Gmbh Verfahren und mittel zum waschen und weichmachen von textilien
US3910855A (en) * 1972-05-16 1975-10-07 Richard M Abeles Liquid cleaning compositions
DE2243306A1 (de) * 1972-09-02 1974-03-21 Henkel & Cie Gmbh Schaumregulierte waschmittel, insbesondere fuer trommelwaschmaschinen
US3959165A (en) * 1972-09-15 1976-05-25 Colgate-Palmolive Company Biodegradable, non-polluting, heavy duty synthetic organic detergent composition
US4028262A (en) * 1972-10-16 1977-06-07 Colgate-Palmolive Company Citrate-carbonate built detergent
US3920563A (en) * 1972-10-31 1975-11-18 Colgate Palmolive Co Soap-cationic combinations as rinse cycle softeners
US3879309A (en) * 1973-01-17 1975-04-22 Louis Gatti Detergent bar made from mixed fatty acid derivatives
US4167561A (en) * 1973-12-28 1979-09-11 Lever Brothers Company Hypochlorite disinfecting compositions and use thereof
US4029607A (en) * 1974-03-29 1977-06-14 The Drackett Company Drain cleaning compositions
DE2703998C3 (de) * 1977-02-01 1981-10-01 Henkel KGaA, 4000 Düsseldorf Flüssiges Waschmittelkonzentrat mit geringem Schaumvermögen
FR2439230A1 (fr) * 1978-10-17 1980-05-16 Seppic Sa Utilisation d'amines grasses pour ameliorer les proprietes des mousses, et les agents moussants ameliores contenant ces amines
FR2440433A1 (fr) * 1978-11-03 1980-05-30 Unilever Nv Composition d'assouplissement des etoffes et procede pour la preparer
EP0026528B2 (de) * 1979-09-29 1992-08-19 THE PROCTER & GAMBLE COMPANY Reinigungsmittelzusammensetzungen
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4492646A (en) * 1980-02-05 1985-01-08 The Procter & Gamble Company Liquid dishwashing detergent containing anionic surfactant, suds stabilizer and highly ethoxylated nonionic drainage promotor
US4561998A (en) * 1982-05-24 1985-12-31 The Procter & Gamble Company Near-neutral pH detergents containing anionic surfactant, cosurfactant and fatty acid
US4460485A (en) * 1983-07-15 1984-07-17 Lever Brothers Company Polyester fabric conditioning and whitening composition
AU570738B2 (en) 1983-10-26 1988-03-24 Unilever Plc Detergent powder
US4686060A (en) * 1986-01-23 1987-08-11 The Procter & Gamble Company Detergent composition providing rinse cycle suds control containing a soap, a quaternary ammonium salt and a silicone
US4637890A (en) * 1986-01-23 1987-01-20 The Procter & Gamble Company Detergent composition providing rinse cycle suds and turbidity control containing a soap, quaternary ammonium salt and a silicone
US4847089A (en) * 1986-07-16 1989-07-11 David N. Kramer Cleansing and distinfecting compositions, including bleaching agents, and sponges and other applicators incorporating the same
US5019280A (en) * 1986-11-14 1991-05-28 The Procter & Gamble Company Ion-pair complex conditioning agent with benzene sulfonate/alkyl benzene sulfonate anionic component and compositions containing same
US4915854A (en) * 1986-11-14 1990-04-10 The Procter & Gamble Company Ion-pair complex conditioning agent and compositions containing same
US4824582A (en) * 1986-11-14 1989-04-25 The Procter & Gamble Company Articles and methods for treating fabrics
US4756850A (en) * 1987-06-10 1988-07-12 The Procter & Gamble Company Articles and methods for treating fabrics
US4913828A (en) * 1987-06-10 1990-04-03 The Procter & Gamble Company Conditioning agents and compositions containing same
US4861502A (en) * 1988-02-08 1989-08-29 The Procter & Gamble Company Conditioning agent containing amine ion-pair complexes and composiitons thereof
US4857213A (en) * 1988-02-08 1989-08-15 The Procter & Gamble Company Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
US5073274A (en) * 1988-02-08 1991-12-17 The Procter & Gamble Co. Liquid detergent containing conditioning agent and high levels of alkyl sulfate/alkyl ethoxylated sulfate
US6210732B1 (en) 2000-02-03 2001-04-03 James A. Papanton Cooking oil additive and method of using
US7244453B1 (en) 2006-01-24 2007-07-17 Lucia Mihalchick Litman Anti-chlorine shampoo composition
AR061906A1 (es) 2006-07-18 2008-10-01 Novapharm Res Australia Limpiador de baja espuma
WO2018128618A1 (en) * 2017-01-05 2018-07-12 Robert Wyne Rapid drying cleaning solution

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US2906712A (en) * 1955-12-13 1959-09-29 Socony Mobil Oil Co Inc Defoamant composition
US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition

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US2932617A (en) * 1956-02-29 1960-04-12 Lever Brothers Ltd Detergent composition containing 2-alkyl-4, 4-bis (hydroxymethyl) oxazolines
US3325414A (en) * 1963-10-01 1967-06-13 Colgate Palmolive Co Heavy duty detergent composition containing a quaternary ammonium salt
GB1066025A (en) * 1964-06-15 1967-04-19 Pyrene Co Ltd Foam-stabilising compositions

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US2954347A (en) * 1955-10-27 1960-09-27 Procter & Gamble Detergent composition
US2906712A (en) * 1955-12-13 1959-09-29 Socony Mobil Oil Co Inc Defoamant composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853779A (en) * 1972-06-06 1974-12-10 Colgate Palmolive Co Low foaming detergent compositions
US3920564A (en) * 1972-09-20 1975-11-18 Colgate Palmolive Co Softener-detergent composition
US4375416A (en) * 1978-11-20 1983-03-01 The Procter & Gamble Company Detergent composition having textile softening properties
US4744911A (en) * 1985-08-01 1988-05-17 The Procter & Gamble Company Dispersible fabric softeners
US5412825A (en) * 1991-10-21 1995-05-09 Samsung Electronics Co., Ltd. Top cover locking system of a boiling clothes washing machine
CN1035276C (zh) * 1991-10-21 1997-06-25 三星电子株式会社 沸水洗衣机的顶盖锁定系统

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US3716499A (en) 1973-02-13
CA949417A (en) 1974-06-18
US3704267A (en) 1972-11-28
DE2126061A1 (de) 1971-12-09
DK138662C (de) 1979-03-19
AT325182B (de) 1975-10-10
DK138662B (da) 1978-10-09
SE382464B (sv) 1976-02-02
CA945037A (en) 1974-04-09
US3714074A (en) 1973-01-30
CA954004A (en) 1974-09-03
NL7107442A (de) 1971-11-30
CA944652A (en) 1974-04-02
US3730912A (en) 1973-05-01
CA945036A (en) 1974-04-09
US3696056A (en) 1972-10-03
CA945034A (en) 1974-04-09
BE767873A (fr) 1971-10-18
CH552053A (de) 1974-07-31
GB1286054A (en) 1972-08-16
FR2093742A5 (de) 1972-01-28

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